(Diethylamino)sulfur trifluoride → HCID 18412755, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[C:6]([C:8]2(O)[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:21])[CH:7]=1.C(N(S(F)(F)[F:41])CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[C:6]([C:8]2([F:41])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:21])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of (±)-3-[5-chloro-2-[4-(trifluoromethyl)phenyl-methoxy]phenyl]-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indole-2-one (Preparation 6, 45 mg, 0.09 mmol) in CH2Cl2 (3 mL), was added dropwise neat diethylaminosulfur trifluoride (0.018 mL, 0.135 mmol) at −78° C. The reaction mixture was warmed to room temperature for 15 minutes and then quenched with water. The organic layer was separated, washed with water, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to provide the title compound (35 mg, 77% yield). MS m/e 502 (MH−). 1H NMR (CDCl3): δ7.84 (d, J=1.95 Hz, 1H), 7.68 (s, 1H), 7.53 (d, J=8.1 Hz, 2H), 7.36 (dd, J=8.7 Hz, 2.5 Hz, 1H), 7.29 (m, 1H), 7.21 (m, 1H), 7.05 (d, J=8.1 Hz, 2H), 6.81(dd, J=8.8 Hz, 1.1 Hz, 1H), 6.73 (s, 1H), 4,88 (d, 11.0 Hz, 1H), 4.73 (d, J=11.0 Hz,1H).