Sodium 3-chlorobenzene-1-sulfinate → Tert-butyl 2-(3-chlorophenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036733Notes

Reaction equation

HRID 2036733 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]=[C:20]([CH3:22])[C:19]2[N:18]([CH3:23])[C:17]3[CH2:24][CH:25]4[NH:29][CH:28]([C:16]=3[C:15]=2[C:14]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]4>>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C:13]2[CH:21]=[C:20]([CH3:22])[C:19]3[N:18]([CH3:23])[C:17]4[CH2:24][CH:25]5[NH:29][CH:28]([C:16]=4[C:15]=3[C:14]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]5)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 23677431Sodium 3-chlorobenzene-1-sulfinateHCID 67085249Tert-butyl 2-bromo-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085162Tert-butyl 2-(3-chlorophenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 39%

Procedure

Intermediate 1 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-chlorophenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (136 mg, 39%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.02 (s, 1H), 7.92 (t, J=1.8 Hz, 1H), 7.83 (dt, J=7.5, 1.5 Hz, 1H), 7.43-7.49 (m, 1H), 7.41 (d, J=7.8 Hz, 1H), 7.33 (s, 1H), 5.22 (br s, 1H), 4.71 (br s, 1H), 3.85 (s, 3H), 3.35 (br s, 1H), 2.76 (s, 3H), 2.45 (d, J=15.9 Hz, 1H), 2.12-2.38 (m, 2H), 1.86-1.97 (m, 1H), 1.52-1.66 (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-9c30886453e946889c4422daed6ef8b5
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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