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

HRID 2036736Notes

Reaction equation

HRID 2036736 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].Br[C:15]1[CH:23]=[C:22]([CH3:24])[C:21]2[N:20]([CH3:25])[C:19]3[CH2:26][CH:27]4[NH:31][CH:30]([C:18]=3[C:17]=2[C:16]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]4>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:15]2[CH:23]=[C:22]([CH3:24])[C:21]3[N:20]([CH3:25])[C:19]4[CH2:26][CH:27]5[NH:31][CH:30]([C:18]=4[C:17]=3[C:16]=2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]5)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 12249756Sodium 4-nitrobenzene-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 67085768Tert-butyl 2-(4-nitro-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 6%

Procedure

Intermediate 12 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-(4-nitro-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (44 mg, 6%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.86-8.33 (m, 2H), 8.08-8.16 (m, 2H), 8.03 (s, 1H), 7.34 (s, 1H), 5.23 (br s, 1H), 4.71 (br s, 1H), 3.85 (s, 3H), 3.36 (br s, 1H), 2.76 (s, 3H), 2.46 (d, J=16.2 Hz, 1H), 2.11-2.39 (m, 2H), 1.85-1.97 (m, 1H), 1.53-1.67 (m, 1H), 1.36 (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-27fbacf7e1a64f9cba2ab909d7fd25a7
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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