3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → HCID 69708557, compound

HRID 2184051Notes

Reaction equation

HRID 2184051 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([F:23])=[C:12]([C:14]3[CH:22]=[N:21][CH:20]=[CH:19][C:15]=3[C:16]([NH2:18])=[O:17])[CH:13]=2)OC1.Br[C:26]1[N:30]2[CH:31]=[CH:32][C:33]([C:35]([F:38])([F:37])[F:36])=[N:34][C:29]2=[N:28][CH:27]=1>>[F:23][C:11]1[CH:10]=[CH:9][C:8]([C:26]2[N:30]3[CH:31]=[CH:32][C:33]([C:35]([F:36])([F:37])[F:38])=[N:34][C:29]3=[N:28][CH:27]=2)=[CH:13][C:12]=1[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17]

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 22473570HCID 22473570, compound

Product 1

HCID 69708557HCID 69708557, compound

Procedure

3-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]isonicotinamide (100 mg, 0.41 mmol) was coupled to 3-bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine (121 mg, 0.46 mmol) using the method in Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 4% methanol, then recrystallisation from toluene, gave 3-[2-fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]isonicotinamide as a yellow solid: δH (400 MHz, d6-DMSO) 7.50-7.60 (3H, m), 7.65 (1H, s), 7.80-7.86 (2H, m), 8.02 (1H, s), 8.30 (1H, s), 8.73-8.76 (2H, m), 9.33 (1H, d, J 7); m/z (ES+) 402 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 4% methanol
  2. customrecrystallisation from toluene

Sources & evidence

ORD record
ord-779060cb7b0a4650808cf4f9e67d6232
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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