3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → HCID 10200631, compound

HRID 2184021Notes

Reaction equation

HRID 2184021 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][C:14]([F:18])=[CH:13][N:12]=1.Br[C:20]1[N:24]2[CH:25]=[CH:26][C:27]([C:29]([F:32])([F:31])[F:30])=[N:28][C:23]2=[N:22][CH:21]=1>>[F:17][C:16]1[C:11]([C:3]2[CH:4]=[C:5]([C:20]3[N:24]4[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[N:28][C:23]4=[N:22][CH:21]=3)[CH:6]=[CH:7][C:2]=2[F:1])=[N:12][CH:13]=[C:14]([F:18])[CH:15]=1

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 116374193-(3,5-Difluoro-pyridin-2-yl)-4-fluorophenylboronic acid

Product 1

HCID 10200631HCID 10200631, compound

Procedure

4-Fluoro-3-(3,5-difluoropyridin-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 2% methanol and crystallisation from toluene/isohexane gave 3-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine: δH (400 MHz, CDCl3) 8.80 (1H, d, J 7), 8.50 (1H, d, J 2), 8.12 (1H, s), 7.79 (1H, dd, J 7 and 2), 7.64 (1H, m), 7.36-7.43 (2H, m), 7.26 (1H, d, J 7); m/z (ES+) 395 (MH+).

Workup

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

Sources & evidence

ORD record
ord-36f64fd10a334bd8bd411dc18aab72e8
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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