2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → 2'-Fluoro-5'-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]biphenyl-2-carbonitrile

HRID 2183874Notes

Reaction equation

HRID 2183874 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: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]([OH:14])([CH3:13])[CH3:12])=[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 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile

Product 1

HCID 99694922'-Fluoro-5'-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]biphenyl-2-carbonitrile

Procedure

2-(3-Bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol 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-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile as an off-white solid: δH (360 MHz, CDCl3) 1.62 (6H, s), 4.50 (1H, s), 7.08 (1H, d, J 7), 7.41 (1H, t, J 9), 7.53-7.64 (4H, m), 7.72 (1H, dd, J 8 and 1), 7.84 (1H, s), 7.86 (1H, s), 8.86 (1H, d, J 7); m/z (ES+) 373 (M++H).

Sources & evidence

ORD record
ord-c3c56e845f764c509667330f74292f08
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

Loading…