3-(Trifluoromethoxy)benzenesulfinic acid sodium salt → Tert-butyl 2-(3-trifluoromethoxy-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036735Notes

Reaction equation

HRID 2036735 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([S:10]([O-:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[Na+].Br[C:17]1[CH:25]=[C:24]([CH3:26])[C:23]2[N:22]([CH3:27])[C:21]3[CH2:28][CH:29]4[NH:33][CH:32]([C:20]=3[C:19]=2[C:18]=1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31][CH2:30]4>>[F:14][C:2]([F:1])([F:13])[O:3][C:4]1[CH:5]=[C:6]([S:10]([C:17]2[CH:25]=[C:24]([CH3:26])[C:23]3[N:22]([CH3:27])[C:21]4[CH2:28][CH:29]5[NH:33][CH:32]([C:20]=4[C:19]=3[C:18]=2[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31][CH2:30]5)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 509987763-(Trifluoromethoxy)benzenesulfinic acid sodium saltHCID 67085249Tert-butyl 2-bromo-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085718Tert-butyl 2-(3-trifluoromethoxy-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 26%

Procedure

Intermediate 3 was coupled to the product of Example 71, step C following the procedure of Example 71, step D. The crude product was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(3-trifluoromethoxy-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (58 mg, 26%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.02 (br s, 1H), 7.85-7.90 (m, 1H), 7.81 (br s, 1H), 7.50 (t, J=8.1 Hz, 1H), 7.31-7.37 (m, 2H), 5.21 (br s, 1H), 4.72 (br s, 1H), 3.85 (s, 3H), 3.35 (br s, 1H), 2.76 (s, 3H), 2.45 (d, J=15.6 Hz, 1H), 2.24-2.49 (m, 1H), 2.12-2.24 (m, 1H), 1.85-1.96 (m, 1H), 1.57-1.66 (m, 1H), 1.37 (br s, 9H).

Workup

  1. customThe crude product was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-02010cedf0cf439a8db236c181d1de20
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

Loading…