2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → HCID 10269219, compound

HRID 2183939Notes

Reaction equation

HRID 2183939 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](B(O)O)=[CH:18][C:17]=1[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=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:25]1[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 22285265HCID 22285265, compound

Product 1

HCID 10269219HCID 10269219, compoundYield 58%

Procedure

2-(3-Bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol was coupled with 4-fluoro-3-(pyridin-4-yl)benzeneboronic acid as described in Example 1 to give 2-[3-(4-fluoro-3-(pyridin-4-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol as a white solid (240 mg, 58%). Bis-hydrochloride salt (from ethyl acetate/ethanol): δH (360 MHz, DMSO) 1.56 (6H, s), 7.77 (1H, dd, J 11 and 9), 7.85 (1H, d, J 7), 7.94-7.98 (1H, m), 8.12-8.15 (3H, m), 8.55 (1H, s), 8.95 (2H, d, J 6), 9.38 (1H, d, J 7); m/z (ES+) 349 (M++H).

Sources & evidence

ORD record
ord-5aa7ff0078c0473494bab4b652abec39
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

Loading…