3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → 4-Fluoro-3'-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 478255Notes

Reaction equation

HRID 478255 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:17]=[C:18]([C:37]#[N:38])[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:23]=2)=[CH:20][CH:21]=1>>[F:15][C:16]1[CH:17]=[C:18]([C:37]#[N:38])[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:2]3[N:6]4[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]4=[N:4][CH:3]=3)[CH:23]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 222853364-Fluoro-3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile

Product 1

HCID 102932394-Fluoro-3'-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrileYield 57%

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-a]pyrimidine was coupled with 4-fluoro-3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 4-fluoro-3′-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile (220 mg, 57%) as a yellow powder: δH (400 MHz, CDCl3) 7.29 (1H, d, J 7), 7.45 (1H, ddd, J 8, 1 and 1), 7.53 (1H, dd, J 8 and 3), 7.55-7.61 (2H, m), 7.65-7.67 (1H, m), 7.70-7.75 (1H, m), 7.77 (1H, s), 8.14 (1H, s), 9.14 (1H, d, J 7); m/z (ES+) 383 (M++H).

Sources & evidence

ORD record
ord-a2d208b4d17b4b4faf3df87de03d25a1
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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