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

HRID 2036717Notes

Reaction equation

HRID 2036717 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]=[CH:22][C:21]2[N:20]([CH3:24])[C:19]3[CH2:25][CH:26]4[NH:30][CH:29]([C:18]=3[C:17]=2[C:16]=1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28][CH2:27]4>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:15]2[CH:23]=[CH:22][C:21]3[N:20]([CH3:24])[C:19]4[CH2:25][CH:26]5[NH:30][CH:29]([C:18]=4[C:17]=3[C:16]=2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28][CH2:27]5)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 12249756Sodium 4-nitrobenzene-1-sulfinateHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085545Tert-butyl 2-(4-nitrophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 54%

Procedure

Intermediate 12 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, 1:1 hexane/ethyl acetate) to give tert-butyl 2-(4-nitrophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (150 mg, 54%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.27-8.31 (m, 2H), 8.19 (s, 1H), 8.09-8.11 (m, 2H), 7.68 (d, J=8.4 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 5.26 (br s, 1H), 4.70 (br s, 1H), 3.62 (s, 3H), 3.40 (br s, 1H), 2.50 (d, J=16.2 Hz, 1H), 2.17-2.31 (m, 2H), 1.89-1.97 (m, 1H), 1.54-1.65 (m, 1H), 1.38 (br s, 9H).

Workup

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

Sources & evidence

ORD record
ord-38c697f16dd74799b3c42977c79ad922
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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