2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → 2-(3-(4-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-a]pyrimidin-7-yl)propan-2-ol

HRID 2183905Notes

Reaction equation

HRID 2183905 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[CH:32]=[N: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[CH:32]=[N: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 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridine

Product 1

HCID 99063092-(3-(4-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-a]pyrimidin-7-yl)propan-2-ol

Procedure

2-(3-Bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol was coupled with 3-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine as described in Example 1 to give 2-[3-(4-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 (400 MHz, DMSO) 1.56 (6H, s), 7.73 (1H, dd, J 11 and 9), 7.81-7.90 (3H, m), 8.09 (1H, dd, J 7 and 2), 8.42 (1H, dd, J 7 and 1), 8.55 (1H, s), 8.81 (1H, dd, J 5 and 1), 9.06 (1H, s), 9.39 (1H, d, J 7).

Sources & evidence

ORD record
ord-fe99fa3994c141d8ac01761544668e09
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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