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

HRID 478228Notes

Reaction equation

HRID 478228 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]([C:27]3[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:24]=[CH:25][CH:26]=2)O1>>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:25]3[CH:24]=[C:23]([C:27]4[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:22]=[CH:21][CH:26]=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 180012803-Bromo-7-methoxyimidazo[1,2-a]pyrimidine

Product 1

HCID 102682453'-(7-Methoxyimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrileYield 66%

Procedure

3-Bromo-7-methoxyimidazo[1,2-a]pyrimidine (0.48 g, 2.12 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-methoxyimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile (458 mg, 66%) as a white powder: δH (400 MHz, CDCl3) 4.08 (3H, s), 6.49 (1H, d, J 7), 7.50 (1H, td, J 8 and 1), 7.51-7.71 (8H, m), 7.81 (1H, dd, J 8 and 1), 8.66 (1H, d, J 7); m/z (ES+) 327 (M++H).

Sources & evidence

ORD record
ord-89b677a203cf47e8a823fd31b56f9452
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

Loading…