Chloroacetone → HCID 87378571, compound

Participants

Reaction Steps

Using a procedure similar to that described in Example 1, except using 2-amino-3-(5,6-dibromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile (60 mg), the title compound was isolated as a white solid (51 mg, 56%). MS (ES): M/Z [M+H]=546. 1H NMR: (400 MHz, DMSO-d6): 1.68 (s, 3H), 5.15 (d, J=13.6 Hz, 1H), 5.16 (d, J=13.6 Hz, 1H), 7.53 (d, J=8.4 Hz, 2H), 7.97 (d, J=8.8 Hz, 2H), 8.74 (s, 1H), 8.78 (s, 1H) and 8.96 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −57.1 (s, 3F). 2-Amino-3-(5,6-dibromo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile (260 mg, 86%; MS (ES): M/Z [M+H]=360) was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(5,6-dibromo-2H-pyrazolo[4,3-b]pyridin-2-yl)propan-2-one (280 mg). 1-(5,6-Dibromo-2H-pyrazolo[4,3-b]pyridin-2-yl)propan-2-one (300 mg) was prepared using a procedure similar to that described in Example 182 part g using chloroacetone and potassium carbonate except starting from 5,6-dibromo-1H-pyrazolo[4,3-b]pyridine (1.18 g). 5,6-Dibromo-1H-pyrazolo[4,3-b]pyridine (1.18 g, 75%) was prepared using a procedure similar to that described in Example 182 part f except starting from 3-amino-5,6-dibromo-2-methylpyridine (1.5 g) and using toluene instead of chloroform. 3-Amino-5,6-dibromo-2-methylpyridine (2.53 g, 89%) was prepared by bromination of 3-amino-5-bromo-2-methylpyridine (2 g, described in Example 182) with N-bromosuccinimide (2.1 g) in acetonitrile (80 mL) at 50° C.

Provenance & Evidence