Category: 1234616-25-1

The important role of 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1234616-25-1, 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1234616-25-1, name is 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.HPLC of Formula: C8H7BrN2

A mixture of 2′-amino-/V,/V-dimethyl-5′-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-[2,3′-bipyridine]-5-carboxamide (360 mg, crude), 4-bromo-l-methyl-pyrrolo[2,3- b]pyridine (103 mg, 0.489 mmol), Na2C03 (2 M in water, 1 mL) and Pd(dppf)Cl2 (36 mg, 0.049 mmol, 10 mol% ) in DME (5 mL) was stirred at 100 C for 16 h under N2 atmosphere. A black suspension was formed. Crude LCMS showed the purity ofproduct is 13% (Rt= 0.513 min; MS Calc?d: 372.1; MS Found: 372.8 [M+H]+). The reaction mixture was diluted with ethyl acetate (10 mL), dried over Na2S04, filtered and concentrated. The residue was purified by Combi Flash (90% EtOAc in pentane), then the impure product was purified by prep-HPLC (0.1% TFA as additive) and lyophilized to afford 2′-amino-/V/V-dimethyl-5′-( 1 -methyl- 1//- pynOlo[2,3-b]pyridin-4-yl)-[2,3′-bipyridine]-5-carboxamide (15.8 mg, yield: 9%) as a light yellow solid. LCMS (Shimadzu LCMS 2010, mobile phase: from 100% [water + 0.05% NH32O] and 0% [MeCN] to 5% [water + 0.05% NH32O] and 95% [MeCN] in 5.8 min, then under this condition for 1.1 min, finally changed to 100% [water + 0.05% NH32O] and 0% [MeCN] and under this condition for 0.09 min.) purity is 97.33%, Rt = 2.472 min; MS Calc?d.: 372.1, MS Found: 373.2 [M+H]+. NMR (400 MHz, CDCh) d 3.11 (3H, s, overlapped with H2O signal), 3.19 (3H, s, overlapped with H2O signal), 4.05 (3H, s), 6.72 (1H, d, J= 3.6 Hz), 7.29 (1H, d , J= 5.2 Hz), 7.40 (1H, d , J= 3.6 Hz), 7.98 (1H, d , J= 8.4 Hz), 8.04 (1H, dd, J= 8.0, 1.6 Hz), 8.37 (1H, s), 8.60 (1H, d , J= 6.4 Hz), 8.61 (1H, s), 8.80 (1H, d, J = 1.6 Hz). 10.27 (2H, br s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1234616-25-1, 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; RAVI, Kannan Karukurichi; LINDSTROeM, Johan; PERSSON, Lars Boukharta; LIVENDAHL, Madeleine; VIKLUND, Jenny; GINMAN, Tobias; FORSBLOM, Rickard; RAHM, Fredrik; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (478 pag.)WO2019/126733; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The important role of 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1234616-25-1, 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1234616-25-1, name is 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.HPLC of Formula: C8H7BrN2

A mixture of 2′-amino-/V,/V-dimethyl-5′-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-[2,3′-bipyridine]-5-carboxamide (360 mg, crude), 4-bromo-l-methyl-pyrrolo[2,3- b]pyridine (103 mg, 0.489 mmol), Na2C03 (2 M in water, 1 mL) and Pd(dppf)Cl2 (36 mg, 0.049 mmol, 10 mol% ) in DME (5 mL) was stirred at 100 C for 16 h under N2 atmosphere. A black suspension was formed. Crude LCMS showed the purity ofproduct is 13% (Rt= 0.513 min; MS Calc?d: 372.1; MS Found: 372.8 [M+H]+). The reaction mixture was diluted with ethyl acetate (10 mL), dried over Na2S04, filtered and concentrated. The residue was purified by Combi Flash (90% EtOAc in pentane), then the impure product was purified by prep-HPLC (0.1% TFA as additive) and lyophilized to afford 2′-amino-/V/V-dimethyl-5′-( 1 -methyl- 1//- pynOlo[2,3-b]pyridin-4-yl)-[2,3′-bipyridine]-5-carboxamide (15.8 mg, yield: 9%) as a light yellow solid. LCMS (Shimadzu LCMS 2010, mobile phase: from 100% [water + 0.05% NH32O] and 0% [MeCN] to 5% [water + 0.05% NH32O] and 95% [MeCN] in 5.8 min, then under this condition for 1.1 min, finally changed to 100% [water + 0.05% NH32O] and 0% [MeCN] and under this condition for 0.09 min.) purity is 97.33%, Rt = 2.472 min; MS Calc?d.: 372.1, MS Found: 373.2 [M+H]+. NMR (400 MHz, CDCh) d 3.11 (3H, s, overlapped with H2O signal), 3.19 (3H, s, overlapped with H2O signal), 4.05 (3H, s), 6.72 (1H, d, J= 3.6 Hz), 7.29 (1H, d , J= 5.2 Hz), 7.40 (1H, d , J= 3.6 Hz), 7.98 (1H, d , J= 8.4 Hz), 8.04 (1H, dd, J= 8.0, 1.6 Hz), 8.37 (1H, s), 8.60 (1H, d , J= 6.4 Hz), 8.61 (1H, s), 8.80 (1H, d, J = 1.6 Hz). 10.27 (2H, br s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1234616-25-1, 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; RAVI, Kannan Karukurichi; LINDSTROeM, Johan; PERSSON, Lars Boukharta; LIVENDAHL, Madeleine; VIKLUND, Jenny; GINMAN, Tobias; FORSBLOM, Rickard; RAHM, Fredrik; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (478 pag.)WO2019/126733; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem