Category: 32111-21-0

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 32111-21-0, name is 2-Iodopyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3IN2

To a solution of 3-nitrophenol (0.151 g, 0.733 mmol) in DMSO (5 mL) was added NaH (35 mg of a 60% dispersion, 0.88 mmol) at 0 C under Ar atmosphere. After stirring for 30 min, 2-iodopyrazine (0.133 mg, 0.953 mmol) was added and mixture heated to 85 C for 4h. To the mixture was added satd. NH4Cl solution (25 mL) and the product extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to yield a crude residue which was purified by column chromatography to afford (97 mg, 61% yield) 2-(3-nitrophenoxy)pyrazine as a white solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 32111-21-0,Some common heterocyclic compound, 32111-21-0, name is 2-Iodopyrazine, molecular formula is C4H3IN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 9 A flask was charged with pinacol borobate (383.0 mg, 1.0 mmol), iodopyrazole (226.6 mg, 1.1 mmol), Pd(OAc)2 (11.2 mg, 0.05 mmol), TFP (46.4 mg, 0.2 mmol), K2CO3 (690.0 mg, 5 mmol), water (3 mL) and DME (2 mL). After 3 vacuum/argon cycles, the resulting mixture was heated to 80 C. 45 min later, HPLC revealed that all boronate disappeared. The area ratio of C-H, coupling product and dimer was about 3.3:85.3:11.4 on HPLC. After the reaction mixture was cooled down to room temperature, EtOAc (5 mL) was added. The aqueous layer was separated and extracted with EtOAc (2*10 mL). The combined organic extracts were washed with brine (10 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified via silica gel chromatography to afford the indole (0.27 g, 81%). 1H NMR (300 HMz, CDCl3) delta 8.77 (2H, bs), 8.60 (1H, s), 8.16 (1H, s), 7.82-7.76 (2H, m), 3.96 (3H, s), 3.78 (3H, s), 3.20 (1H, m), 2.08-1.92 (6H, m), 1.72-1.69 (2H, m); 13C NMR (100 HMz, CDCl3) delta 168.0, 147.4, 146.6, 144.4, 143.2, 138.0, 135.3, 129.0, 124.2, 120.5, 120.3, 120.0, 112.4, 52.0, 37.3, 33.6, 31.3, 26.5.

The synthetic route of 32111-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/183752; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 32111-21-0 as follows. HPLC of Formula: C4H3IN2

Example 42; Synthesis of Compound 76; Compound a from the synthesis of compound 74 (255 mg) was placed in an oven dried microwave reaction vial with CuI (53.3 mg) and K3PO4 (233.4 mg) and purged with N2. To this mixture was added iodopyrazine b and the vial purged again with N2 followed by addition of 1,2-cyclohexanediamine (62.8 mg) in 2.6 ml dioxane and N2 was bubbled into the solution for 10 min and the vial crimped. The reaction vial was placed in the microwave for 30 min. at 140 C. The reaction went to half completion and was worked up by filtering off the non-product solids, concentrating under vacuum, and purifying by flash to give 139 mg compound c (47% yield). Compound c was dissolved in 3 ml 1.0 M TBAF in THF and heated to 60 C. overnight. The reaction was completed by LCMS and was diluted with H2O, extracted with EtOAc, washed with brine, dried over MgSO4, concentrated under vacuum and purified by SFC to give the final compound 76.

According to the analysis of related databases, 32111-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rawson, Thomas E.; Safina, Brian; Dotson, Jennafer; Zhou, Aihe; Aliagas-Martin, Ignacio; Halladay, Jason; Liang, Jun; Rueth, Matthias; Zhu, Bing-Yan; US2007/37791; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 32111-21-0,Some common heterocyclic compound, 32111-21-0, name is 2-Iodopyrazine, molecular formula is C4H3IN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 58; N- f 3-[” 1 -(4-Chloro-phenvU-6-oxo-2-( 4-pyrazin-2-yl-phenylV 1.6-dihvdro-purin-9-yll-phenyl – methane sulfonamide; [00193] A solution of N-(3-{l-(4-chloro-phenyl)-6-oxo-2-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-l,6-dihydro-purin-9-yl}-phenyl)-methane sulfonamide (preparaed as described in example 26, 0.5 g, 0.809 mmol) in N,N-dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.25 g, 1.21 tnmol), cesium carbonate (0.527 g, 1.61 mmol), Pd(dppf)2Cl2 (0.059 g, 0.08 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is stirred at rt for 18 h. The reaction mixture is poured into water and extracted with ethyl acetate (3 *). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by column chromatography to afford N-{3-[l-(4-chloro-phenyl)-6-oxo-2-(4-pyrazin-2-yl-phenyl)-l ,6- dihydro-purin-9-yl]-phenyl}-methane sulfonamide. 1H NMR (DMSOd6, 400 MHz) delta 9.25 (s, IH), 8.69 (m, IH), 8.62 (m, 2H), 8.03 (m, 2H), 7.74 (s, IH), 7.46-7.56 (m, 9H), 7.25 (m, IH), 3.05 (s, 3H); LC-MS calculated for C28H20ClN7O3S (M+H4) 570.1, found 569.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodopyrazine, its application will become more common.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 32111-21-0, name is 2-Iodopyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H3IN2

To a solution of 3-nitrophenol (0.151 g, 0.733 mmol) in DMSO (5 mL) was added NaH (35 mg of a 60% dispersion, 0.88 mmol) at 0 C under Ar atmosphere. After stirring for 30 min, 2-iodopyrazine (0.133 mg, 0.953 mmol) was added and mixture heated to 85 C for 4h. To the mixture was added satd. NH4Cl solution (25 mL) and the product extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to yield a crude residue which was purified by column chromatography to afford (97 mg, 61% yield) 2-(3-nitrophenoxy)pyrazine as a white solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference of 32111-21-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 32111-21-0, name is 2-Iodopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step B: A solution of 3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[l,3,2]-dioxa-borolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl}-benzene sulfonamide (2, 0.650 g, 1.08 mmol).in.N,N-dimethylformamide (10 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.33 g, 1.616 mmol), cesium carbonate (0.701 g, 2.15 mmol), Pd(dppf)2Cl2 (0.087 g, 0.107 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 100 0C for 2.5 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3 *). The combined organic layer is washed with brine, dried over Na2SC>4, concentrated, and purified by preparative HPLC to afford 3-[5-(4-chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5- dihydro-pyrazolo[3,4-d]pyrimidin-l-yl]-benzene sulfonamide (3). 1H NMR (DMSO-d6, 400 MHz) delta 9.25 (s, IH), 8.71 (m, IH), 8.63 (d, IH), 8.58 (m, 2H), 8.45 (m, IH), 8.07 (m, 2H)5 7.80 (m, 2H), 7.59 (m, 4H), 7.45 (m, 4H); LC-MS calculated for C27H18C1N7O3S (M+H*) 556.1, found 555.9.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Iodopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 32111-21-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 32111-21-0, name is 2-Iodopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

4.4 ml of tetrabutylammonium fluoride (1M solution in THF) are added to a solution of 450 mg (2.18 mmol) of iodopyrazine, 647 mg (3.28 mmol) of 5-chloro-3-methoxy-2-(prop-2-ynyloxy)-pyridine (Example P7), 83 mg (0.44 mmol) of copper(l) iodide and 153 mg (0.22 mmol) of bis(triphenylphosphine)palladium dichloride (Pd(PPh3)2CI2) in 14 ml of dioxane. The reaction mixture is stirred for 3 hours at 50C under an argon atmosphere and is then allowed to cool to 20C. The solvent is removed under reduced pressure and the crude product obtained is purified by means of flash chromatography (eluant: ethyl acetate/petroleum ether 1/2). The desired title compound is obtained as a brown solid having a melting point of 142C in a yield of 510 mg (84 % of theory). Rf = 0.50 in ethyl acetate/petroleum ether 1/1;1H NMR (CDCI3): delta(ppm)= 3.89 (s, 3H); 5.29 (s, 2H); 7.08 (d, J=2.2 Hz, 1H); 7.71 (d, J=2.2 Hz, 1H); 8.48 (d, J=2.5 Hz, 1H); 8.52 (dxd, J=1.3 and 2.5 Hz, 1H); 8.66 (d, J=1.3 Hz, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Iodopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2003/104206; (2003); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 32111-21-0,Some common heterocyclic compound, 32111-21-0, name is 2-Iodopyrazine, molecular formula is C4H3IN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of N- (5-chloro-7-ethynyl-1, 3-benzodioxol-4-yl)-6-methoxy-7- (3- morpholin-4-ylpropoxy) quinazolin-4-amine (0.12g, 0. 24mmol), 3-iodopyrazine (O. lg, 0. 48mmol) and diisopropylamine (0. 066ml, 0. 48mmol) in ethyl acetate (3ml) was cooled to- 20 C under a nitrogen atmosphere. To this was added copper (I) iodide (0.014g, 0.072mmol) and bis (triphenylphospine) palladium (It) chloride (0.034g, 0. 048mmol). The reaction mixture was allowed to warm to ambient temperature and then stirred overnight. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography on silica eluting with a mixture of 0-10% methanol in dichloromethane to give the product as a light yellow solid (0.052g, 38%). NMR Spectrum: (DMSOd6) 1.99 (t, 2H), 2.40 (brs, 4H), 2.50 (t, 2H) partially obscured by DMSO peak, 3.59 (s, 4H), 3.97 (s, 3H), 4.23 (t, 2H), 6.27 (s, 2H), 7.19 (s, 1H), 7.35 (s, 1H), 7.89 (s, 1H), 8.42 (s, 1H), 8.74 (s, 1H), 8.78 (s, 1H), 8.96 (s, 1H), 9.66 (s, 1H). Mass Spectrum: M+H+ 575 and M+H-573.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodopyrazine, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/4732; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 32111-21-0, name is 2-Iodopyrazine, belongs to Pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32111-21-0, Quality Control of 2-Iodopyrazine

Example 55; N-(3-(5-(4-chlorophenyl’>-4-oxo-6-f4-fpyrazin-2-vDphenyl’)-4.5-dihvdro- 1 H-pyrazolof 3.4- d]p yrirnidin- 1 -yDphenyPmethanesulfonamide; [00189] A solution of N-(3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[ 1 ,3,2]dioxa-borolan-2-yl)phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyriinidin-l -yl} -phenyl)- methane sulfonamide (prepared as described in example 35, 0.50 g, 0.81 mmol) in N,N- dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.25 g, 1.21 mmol), cesium carbonate (0.527 g, 1.61 mmol), Pd(dppf)2Cl2 (0.06 g, 0.082 mmol) are added and the resulting solution is degassed with argon for 0.5 h. The reaction mixture is then heated at 100 0C for 3 h. The reaction mixture is cooled to it and diluted with water and extracted with ethyl acetate (3 *). The combined organic layer is washed with brine, dried over Na2SO-I, concentrated, and purified by column chromatography to afford N-{3-[5-(4- chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5-dihydro-pytauazolo[3 ,4-d]pyrimidin- 1 -yl]- phenyl} -methane sulfonamide. 1H NMR (DMSO-d6, 400 MHz) delta 10.15 (br, 1 H), 9.26 (d, IH), 8.71 (d, IH), 8.62 (d, IH), 8.52 (s, IH), 8.06 (m, 3H), 7.82 (m, IH), 7.60 (m, 2H), 7.52 (m, IH), 7.40 (m, 4H), 7.18 (m, IH), 3.02 (s, 3H); LC-MS calculated for C28H20ClN7O3S (M+H+) 570.1, found 570.0.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 32111-21-0, A common heterocyclic compound, 32111-21-0, name is 2-Iodopyrazine, molecular formula is C4H3IN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 47; S-fS^-Chloro-phenyl^-oxo–^-pyrazin-?-yl-pheny?^.S-dihvdro-pyrazolorB^-dipyrimidin- 1 -yll-benzonitrile; [00175] A solution of 3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4 ,4,5,5-tetramethyl-[l ,3,2]- dioxaborolan-2-yl)-phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl}-benzonitrile (prepared as described in example 28, 3.6 g, 6.54 mmol) in N,N-dimethylformamide (70 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (2.0 g, 9.82 mmol), cesium carbonate (4.2 g, 13.09 mmol), Pd(dppf)2Cl2 (0.53 g, 0.654 mmol) is added and the resulted mixture is degassed with argon for 0.5 h The reaction mixture is then heated at 100 0C for 1.5 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3 x). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by column chromatography to afford 3-[5-(4-chloro-phenyl)-4-oxo-6-(4-pyrazin-2- yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-l-yl]-benzonitrile. 1H NMR (DMSO-dbeta, 400 MHz) delta 9.25 (s, IH), 8.71 (m, IH), 8.62 (m, 2H), 8.51 (m, 2H), 8.08 (d, 2H), 7.90 (m, IH), 7.88 (m, IH), 7.60 (d, 2H), 7.44 (m, 4H); LC-MS calculated for C28H16ClN7O (M+H+) 502.1, found 502.0.

The synthetic route of 32111-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem