3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → HCID 10134101, compound

HRID 2183982Notes

Reaction equation

HRID 2183982 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[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[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 22329529HCID 22329529, compound

Product 1

HCID 10134101HCID 10134101, compound

Procedure

4-Fluoro-3-(5-fluoropyridin-2-yl)phenylboronic acid was coupled with 3-bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine by the method of Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 3.5% methanol, then crystallisation from hot toluene/isohexane and further crystallisation from hot methanol, gave 3-[4-fluoro-3-(5-fluoropyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine: δH (400 MHz, DMSO) 9.28 (1H, d, J 7), 8.76 (1H, d, J 3), 8.30 (1H, s), 8.20 (1H, dd, J 7 and 2), 7.88 (3H, m), 7.62 (1H, dd, J 11 and 9), 7.53 (1H, d, J 7).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 3.5% methanol
  2. customcrystallisation
  3. customfrom hot toluene/isohexane and further crystallisation from hot methanol

Sources & evidence

ORD record
ord-b965f93ad26f494a99d2c083517e6278
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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