3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → HCID 10292904, compound

HRID 2183935Notes

Reaction equation

HRID 2183935 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](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=[C:18]([F:31])[C:17]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1>>[F:15][C:16]1[C:17]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[C:18]([F:31])[CH:19]=[CH:20][C:21]=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 224735672-[2,6-Difluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine

Product 1

HCID 10292904HCID 10292904, compound

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 2-[2,6-difluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine as described in Example 1 to give 3-[2,4-difluoro-3-(pyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a pale yellow solid. Bis-hydrochloride salt (from ethyl acetate/ethanol): δH (360 MHz, DMSO) 7.55 (1H, dd, J 9 and 9), 7.62-7.68 (2H, m), 7.86-7.96 (2H, m), 8.14 (1H, ddd, J 8, 8 and 2), 8.38 (1H, s), 8.84 (1H, d, J 5), 9.30 (1H, dd, J 7 and 3); m/z (ES+) 377 (M++H).

Sources & evidence

ORD record
ord-42b83c51912e4b98bc9cb84571e9b76d
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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