Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)(=[O:11])=[O:10].Cl[C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:23]=[C:22]([S:30][CH3:31])[N:21]=1.[F-].[K+]>C(#N)C>[CH3:31][S:30][C:22]1[N:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:25]=[C:20]([N:14]2[CH2:15][CH2:16][C@H:12]([S:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:17])([F:1])[F:18])(=[O:11])=[O:10])[CH2:13]2)[N:21]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-3-(2-Trifluoromethyl-benzenesulfonyl)-pyrrolidine (500 mg) was dissolved in acetonitrile (3.5 mL) in a microwave tube. 4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine (450 mg), TEA (0.75 mL) and KF (10 mg) were added. The reaction mixture was irradiated in the microwave oven at 150° C. for 1.5 h. The reaction mixture was evaporated to dryness and purified by flash chromatography (50 g silica gel, ethyl acetate/n-heptane:0:1→1:0) to yield a light yellow oil (790 mg; 94%) MS: m/z=472.2 [M+H]+.
Workup
- customThe reaction mixture was irradiated in the microwave oven at 150° C. for 1.5 h
- customThe reaction mixture was evaporated to dryness
- custompurified by flash chromatography (50 g silica gel, ethyl acetate/n-heptane:0:1→1:0)
- customto yield a light yellow oil (790 mg; 94%)
Sources & evidence
- ORD record
- ord-426f1c2152a64c8bbebd23636fbb52b5
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524710B2
Linked notes
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