2,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid → 3-[2,4-Difluoro-3-(pyridin-3-yl)phenyl]-7-(1-fluoro-1-methylethyl)imidazo[1,2-alpha]pyrimidine

HRID 2184033Notes

Reaction equation

HRID 2184033 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F: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)=[C:20]([F:28])[CH:19]=[CH:18][C:17]=1B(O)O>>[F:28][C:20]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:16]([F:15])[CH:17]=[CH:18][C:19]=1[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 222400962,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acidHCID 695605543-Bromo-7-(1-fluoro-1-methylethyl)imidazo[1,2-alpha]pyrimidine

Product 1

HCID 101558713-[2,4-Difluoro-3-(pyridin-3-yl)phenyl]-7-(1-fluoro-1-methylethyl)imidazo[1,2-alpha]pyrimidine

Procedure

3-Bromo-7-(1-fluoro-1-methylethyl)imidazo[1,2-α]pyrimidine was coupled to 2,4-difluoro-3-(pyridin-3-yl)phenylboronic acid as described in Example 65 to afford 3-[2,4-difluoro-3-(pyridin-3-yl)phenyl]-7-(1-fluoro-1-methylethyl)imidazo[1,2-α]pyrimidine as a white solid: δH (360 MHz, CDCl3) 1.80 (6H, d, J 22), 7.21-7.29 (2H, m), 7.46 (1H, dd, J 8 and 5), 7.50-7.57 (1H, m), 7.85 (1H, d, J 8), 7.92 (1H, s), 8.31 (1H, dd, J 7 and 3), 8.70 (1H, dd, J 5 and 1), 8.79 (1H, s); m/z (ES+) 369 (M++H).

Sources & evidence

ORD record
ord-435101344c8c4703b90122d2953748cc
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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