2-(Trifluoromethyl)benzeneboronic acid → HCID 9946553, compound

HRID 478243Notes

Reaction equation

HRID 478243 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[N:3]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[C:26]([F:37])([F:36])[F:25])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[N:3]=1

Participants

3

Reactant 2

HCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 86759229HCID 86759229, compound

Product 1

HCID 9946553HCID 9946553, compoundYield 35.4%

Procedure

Trifluoromethanesulfonic acid 3-(7-methylimidazo[1,2-a]pyrimidin-3-yl)phenyl ester (0.1 g, 0.28 mmol) was coupled to 2-trifluoromethylbenzeneboronic acid (52 μl, 0.59 mmol) as described in Example 21 to give 7-methyl-3-(2′-trifluoromethylbiphenyl-3-yl)-imidazo[1,2-a]pyrimidine as a white solid (35 mg): δH (400 MHz, CDCl3) 2.65 (3H, s), 6.77 (1H, d, J 7), 7.39 (1H, m), 7.48-7.62 (6H, m), 7.78 (1H, d, J 7.2), 7.82 (1H, s), 8.52 (1H, d, J 7); m/z (ES+) 354 (M++H).

Sources & evidence

ORD record
ord-c7baebaa99994c049fa98f79561bd591
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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