3'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile → 3-(7-Trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 478221Notes

Reaction equation

HRID 478221 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.CC1(C)C(C)(C)OB([C:23]2[CH:24]=[C:25]([C:29]3[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:26]=[CH:27][CH:28]=2)O1>>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:27]3[CH:26]=[C:25]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:24]=[CH:23][CH:28]=3)=[CH:3][N:4]=[C:5]2[N:10]=1

Participants

3

Reactant 2

HCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine

Product 1

HCID 99252683-(7-Trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrileYield 44%

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-a]pyrimidine (0.28 g, 1.04 mmol) was coupled with 3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 3′-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile (165 mg, 44%) as a yellow powder: δH (400 MHz, CDCl3) 7.29 (1H, d, J 7), 7.53 (1H, td, J 8 and 1), 7.59-7.68 (3H, m), 7.70-7.75 (2H, m), 7.80-7.85 (2H, m), 8.14 (1H, s), 9.20 (1H, d, J 7); m/z (ES+) 365 (M++H).

Sources & evidence

ORD record
ord-063427371b06443987d9368b247abf3c
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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