Sodium 4-(trifluoromethyl)benzene-1-sulfinate → Tert-butyl 2-(4-trifluoromethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[Na+].Br[C:16]1[CH:24]=[CH:23][C:22]2[N:21]([CH3:25])[C:20]3[CH2:26][CH:27]4[NH:31][CH:30]([C:19]=3[C:18]=2[C:17]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]4>>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:16]2[CH:24]=[CH:23][C:22]3[N:21]([CH3:25])[C:20]4[CH2:26][CH:27]5[NH:31][CH:30]([C:19]=4[C:18]=3[C:17]=2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]5)(=[O:11])=[O:10])=[CH:7][CH:8]=1Participants
3
Reactant 2
Product 1
Procedure
Intermediate 17 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude product was purified by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate) to give tert-butyl 2-(4-trifluoromethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (130 mg, 24%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.19 (s, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.67-7.78 (m, 3H), 7.31-7.33 (m, 1H), 5.30 (br s, 1H), 4.70 (br s, 1H), 3.58 (s, 3H), 3.37-3.41 (m, 1H), 2.51 (d, J=16.3 Hz, 1H), 2.16-2.31 (m, 2H), 1.90-1.96 (m, 1H), 1.56-1.65 (m, 1H), 1.37 (s, 9H).
Workup
- customThe crude product was purified by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-85c86280bd984f6db57f518f01b5a805
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575186B2
Reaction notes
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