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

HRID 2036734Notes

Reaction equation

HRID 2036734 reaction equation
[CH3:1][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>>[CH3:1][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 23703014Sodium 3-methylbenzene-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 67085626Tert-butyl 2-(3-methyl-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 29%

Procedure

Intermediate 10 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-methyl-phenyl)sulfonyl-4,5-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (85 mg, 29%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.97-8.05 (m, 1H), 7.71-7.78 (m, 2H), 7.29-7.38 (m, 3H), 5.23 (br s, 1H), 4.72 (br s, 1H), 3.83 (s, 3H), 3.33 (br s, 1H), 2.74 (s, 3H), 2.45 (d, J=16.2 Hz, 1H), 2.38 (s, 3H), 2.11-2.35 (m, 2H), 1.88-1.97 (m, 1H), 1.55-1.64 (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-688f5f8412f342f19fe3439468e5ae84
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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