2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → 2-[3-(2-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

HRID 2183943Notes

Reaction equation

HRID 2183943 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[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>>[F:15][C:16]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:20][CH:19]=[CH:18][C:17]=1[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

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 222853162-Fluoro-3-(pyridin-3-yl)phenylboronic acid

Product 1

HCID 101324742-[3-(2-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

Procedure

2-(3-Bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol was coupled with 2-fluoro-3-(pyridin-3-yl)benzeneboronic acid as described in Example 1 to give 2-[3-(2-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol as a white solid. Bis-hydrochloride salt (from ethyl acetate/ethanol): δH (360 MHz, DMSO) 1.56 (6H, s), 7.65 (1H, dd, J 8 and 8), 7.79-7.83 (1H, m), 7.85-7.87 (2H, m), 7.92-7.97 (1H, m), 8.48 (1H, d, J 7), 8.55 (1H, s), 8.83 (1H, dd, J 5 and 1), 9.10 (1H, s), 9.29 (1H, dd, J 7 and 3); m/z (ES+) 349 (M++H).

Sources & evidence

ORD record
ord-aefe610c69474610869abc7a2d9deff7
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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