2-Bromo-1-pyridin-1-ium-3-ylethanone bromide → HCID 9968105, compound
Reaction equation
[Br-].Br[CH2:3][C:4]([C:6]1[CH:7]=[NH+:8][CH:9]=[CH:10][CH:11]=1)=O.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:19]=[CH:18][N:17]2[C:20]([C:23](=[S:25])[NH2:24])=[CH:21][N:22]=[C:16]2[N:15]=1>CN(C=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4]2[N:24]=[C:23]([C:20]3[N:17]4[CH:18]=[CH:19][C:14]([C:13]([F:27])([F:26])[F:12])=[N:15][C:16]4=[N:22][CH:21]=3)[S:25][CH:3]=2)[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
3-(Bromoacetyl)pyridinium bromide (41 mg, 0.14 mmol) was added to a stirred solution of the foregoing thioamide (24 mg, 0.1 mmol) in DMF (1 ml) at room temperature under N2. The reaction was warmed to 60° C. for 1 h and then concentrated under reduced pressure while azeotroping with xylene (20 ml). The crude residue was taken up in EtOAc (50 ml), washed with saturated sodium hydrogencarbonate solution (20 ml) and concentrated under reduced pressure while dry loading onto silica. Subsequent purification by column chromatography on silica using 70% EtOAc in hexanes containing 1% Et3N and 1% MeOH as the eluent gave 3-[4-(pyridin-3-yl)thiazol-2-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine (33 mg, 97%): δH (400 MHz, d6-DMSO) 7.52-7.60 (1H, m), 7.80 (1H, d, J 7.1), 8.43 (1H, s), 8.50 (1H, dt, J 7.8 and 2.0), 8.62 (1H, m), 8.83 (1H, s), 9.39 (1H, s), 10.33 (1H, d, J 7.1); m/z (ES+) 347 (M+).