Sodium 3-chlorobenzene-1-sulfinate → Tert-butyl 2-(3-chlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036694Notes

Reaction equation

HRID 2036694 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Na+].Br[C:13]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3[CH2:23][CH:24]4[NH:28][CH:27]([C:16]=3[C:15]=2[C:14]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]4>>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]5)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 23677431Sodium 3-chlorobenzene-1-sulfinateHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085979Tert-butyl 2-(3-chlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 35%

Procedure

Intermediate 1 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude material was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(3-chlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (110 mg, 35%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.17-8.23 (m, 1H), 7.92-7.96 (m, 1H), 7.83-7.88 (m, 1H), 7.65-7.73 (m, 1H), 7.46-7.50 (m, 1H), 7.41 (t, J=7.8 Hz, 1H), 7.34 (d, J=8.7 Hz, 1H), 5.20-5.36 (m, 1H), 4.60-4.73 (m, 1H), 3.63 (s, 3H), 3.30-3.50 (m, 1H), 2.52 (d, J=16.2 Hz, 1H), 2.15-2.42 (m, 2H), 1.90-2.01 (m, 1H), 1.58-1.60 (m, 1H), 1.39 (br s, 9H)

Workup

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

Sources & evidence

ORD record
ord-72c53b4e801844678b8ba10d35bdff86
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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