5-methyl-2-(trifluoromethyl)furan-3-sulfonyl Chloride → HCID 57901600, compound
Reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].[CH3:16][C:17]1[O:21][C:20]([C:22]([F:25])([F:24])[F:23])=[C:19]([S:26](Cl)(=[O:28])=[O:27])[CH:18]=1>N1C=CC=CC=1>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][S:26]([C:19]1[CH:18]=[C:17]([CH3:16])[O:21][C:20]=1[C:22]([F:25])([F:23])[F:24])(=[O:28])=[O:27]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine (100 mg) and pyridine (3 mL) was added 5-methyl-2-trifluoromethylfuran-3-sulfonyl chloride (150 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (90 mg, yield 46%) as pale-yellow crystals. M+1=430.