3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → HCID 9970131, compound

HRID 2183882Notes

Reaction equation

HRID 2183882 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[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:17]=1[C:31]1[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=1>>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:18][C:17]=1[C:31]1[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile

Product 1

HCID 9970131HCID 9970131, compound

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 2′-fluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile as a yellow powder: δH (400 MHz, CDCl3) 7.29 (1H, d, J 7), 7.45 (1H, t, J 8), 7.56 (1H, ddd, J 8, 8 and 1), 7.62-7.68 (3H, m), 7.70 (1H, ddd, J 8, 8 and 1), 7.85 (1H, dd, J 8 and 1), 8.10 (1H, s), 9.06 (1H, d, J 7); m/z (ES+) 383 (M++H).

Sources & evidence

ORD record
ord-6d60bc45764d470db3194da742020425
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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