2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → 4-Fluoro-3'-[7-(2-hydroxyprop-2-yl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile

HRID 478256Notes

Reaction equation

HRID 478256 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[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]([OH:14])([CH3:13])[CH3:12])=[N:10][C:5]4=[N:4][CH:3]=3)[CH:23]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 222853364-Fluoro-3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile

Product 1

HCID 101338564-Fluoro-3'-[7-(2-hydroxyprop-2-yl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrileYield 70%

Procedure

2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol 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-(2-hydroxyprop-2-yl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile (260 mg, 70%) as a yellow powder: δH (360 MHz, CDCl3) 1.61 (6H, s), 4.51 (1H, s), 7.07 (1H, d, J 7), 7.45 (1H, ddd, J 8, 1 and 1), 7.51-7.60 (3H, m), 7.63-7.69 (2H, m), 7.73 (1H, s), 7.90 (1H, s), 8.94 (1H, d, J 7); m/z (ES+) 383 (M++H).

Sources & evidence

ORD record
ord-4efc799982314db0abb04a182d8b9304
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

Loading…