3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → HCID 10199517, compound

HRID 2184015Notes

Reaction equation

HRID 2184015 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][N:12]=1.Br[C:19]1[N:23]2[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[N:27][C:22]2=[N:21][CH:20]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2[N:23]3[CH:24]=[CH:25][C:26]([C:28]([F:29])([F:30])[F:31])=[N:27][C:22]3=[N:21][CH:20]=2)=[CH:4][C:3]=1[C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 11593861HCID 11593861, compound

Product 1

HCID 10199517HCID 10199517, compound

Procedure

4-Fluoro-3-(3-fluoropyridin-2-yl)phenylboronic acid was coupled with 3-bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine by the method of Example 78. Purification by chromatography on silica gel eluting with dichloromethane containing 3.5% methanol and crystallisation from methanol gave 3-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine: δH (400 MHz, DMSO) 9.28 (1H, d, J 7), 8.61 (1H, m), 8.31 (1H, s), 7.90-7.99 (3H, m), 7.62 (2H, m), 7.52 (1H, d, J 7); m/z (ES+) 377 (MH+).

Workup

  1. customPurification by chromatography on silica gel eluting
  2. customwith dichloromethane containing 3.5% methanol and crystallisation from methanol

Sources & evidence

ORD record
ord-4ca684e63f434030a04ec970e6119134
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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