3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → 3-[2,4-Difluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-alpha]pyrimidine

HRID 2183933Notes

Reaction equation

HRID 2183933 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:20]([F:28])[CH:19]=[CH:18][C:17]=1B(O)O>>[F:28][C:20]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:16]([F:15])[CH:17]=[CH:18][C:19]=1[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 222400962,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid

Product 1

HCID 101341003-[2,4-Difluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-alpha]pyrimidine

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 2,4-difluoro-3-(pyridin-3-yl)benzeneboronic acid as described in Example 1 to give 3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as an off-white solid. Bis-hydrochloride salt (from ethyl acetate/ethanol): δH (400 MHz, DMSO) 7.60-7.65 (2H, m), 7.90-7.96 (2H, m), 8.34 (1H, s), 8.47 (1H, d, J 8), 8.87 (1H, dd, J 5 and 1), 9.08 (1H, s), 9.32 (1H, dd, J 7 and 3).

Sources & evidence

ORD record
ord-ee7341c77e7246ab99875d64a0a060f4
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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