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

HRID 2183946Notes

Reaction equation

HRID 2183946 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:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>>[F:15][C:16]1[C:21]([C:22]2[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=2)=[CH:20][CH:19]=[CH:18][C:17]=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 22285310[2-Fluoro-3-(pyridin-4-yl)phenyl]boronic acid

Product 1

HCID 102697513-[2-Fluoro-3-(pyridin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-alpha]pyrimidine

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 2-fluoro-3-(pyridin-4-yl)benzeneboronic acid as described in Example 1 to give 3-[2-fluoro-3-(pyridin-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a white solid. Bis-hydrochloride salt (from ethyl acetate/ethanol): δH (400 MHz, DMSO) 7.64-7.70 (2H, m), 7.95-8.01 (2H, m), 8.37 (1H, s), 8.39 (2H, s), 9.05-9.07 (2H, m), 9.40 (1H, dd, J 7 and 3); m/z (ES+) 359 (M++H).

Sources & evidence

ORD record
ord-492af667be1d4091bb46283465872191
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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