3-bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → HCID 69708193, compound

HRID 2184060Notes

Reaction equation

HRID 2184060 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([F:19])=[C:12]([N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)[CH:13]=2)OC1.Br[C:22]1[N:26]2[CH:27]=[CH:28][C:29]([C:31]([F:34])([F:33])[F:32])=[N:30][C:25]2=[N:24][CH:23]=1>>[F:19][C:11]1[CH:10]=[CH:9][C:8]([C:22]2[N:26]3[CH:27]=[CH:28][C:29]([C:31]([F:32])([F:33])[F:34])=[N:30][C:25]3=[N:24][CH:23]=2)=[CH:13][C:12]=1[N:14]1[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

3

Reactant 2

HCID 113914623-bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 223294941-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-1H-pyrazole

Product 1

HCID 69708193HCID 69708193, compound

Procedure

1-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-1H-pyrazole (300 mg, 1.0 mmol) was coupled to 3-bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine (266 mg, 1.0 mmol) using the method in Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 1% methanol, then recrystallisation from toluene/isohexane, gave 3-[4-fluoro-3-(pyrazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 6.55 (1H, dd, J 3 and 2), 7.28 (1H, d, J 7), 7.44-7.47 (2H, m), 7.77 (1H, d, J 2), 8.13-8.15 (2H, m), 8.21-8.24 (1H, m), 8.85 (1H, d, J 7); m/z (ES+) 348 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 1% methanol
  2. customrecrystallisation from toluene/isohexane

Sources & evidence

ORD record
ord-b93a56065b2b4857837485e965cb4c91
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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