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

HRID 2183942Notes

Reaction equation

HRID 2183942 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)=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>>[F:15][C:16]1[C:21]([C:22]2[CH:23]=[N:24][CH: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 222853162-Fluoro-3-(pyridin-3-yl)phenylboronic acid

Product 1

HCID 101330073-[2-Fluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-alpha]pyrimidine

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 2-fluoro-3-(pyridin-3-yl)benzeneboronic acid as described in Example 1 to give 3-[2-fluoro-3-(pyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as an off-white solid. Bis-hydrochloride salt (from ethyl acetate/ethanol): δH (360 MHz, DMSO) 7.62 (2H, dd, J 7 and 7), 7.85-7.96 (3H, m), 8.36 (1H, s), 8.58 (1H, d, J 8), 8.86 (1H, dd, J 5 and 1), 9.14 (1H, s), 9.33 (1H, dd, J 7 and 3); m/z (ES+) 359 (M++H).

Sources & evidence

ORD record
ord-5befec7aef094b118dd30199f8f6fce8
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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