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

HRID 2036685Notes

Reaction equation

HRID 2036685 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[Na+].Br[C:14]1[CH:22]=[CH:21][C:20]2[N:19]([CH3:23])[C:18]3[CH2:24][CH:25]4[NH:29][CH:28]([C:17]=3[C:16]=2[C:15]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]4>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:14]2[CH:22]=[CH:21][C:20]3[N:19]([CH3:23])[C:18]4[CH2:24][CH:25]5[NH:29][CH:28]([C:17]=4[C:16]=3[C:15]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]5)(=[O:11])=[O:10])=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 23668300Sodium 4-cyanobenzenesulfinateHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085455Tert-butyl 2-(4-cyanophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 50%

Procedure

Intermediate 11 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude product was purified by flash column chromatography (SiO2, 8:2 hexane/ethyl acetate) to give tert-butyl 2-(4-cyanophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (184 mg, 50%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.18 (s, 1H), 8.05 (dd, J=6.9, 1.5 Hz, 2H), 7.75 (dd, J=6.9, 1.5 Hz, 2H), 7.66 (dd, J=8.7, 1.5 Hz, 1H), 7.33 (d, J=8.7 Hz, 1H), 5.26 (br s, 1H), 4.69 (br s, 1H), 3.62 (s, 3H), 3.37 (br s, 1H), 2.51 (d, J=15.9 Hz, 1H), 2.13-2.41 (m, 2H), 1.87-1.99 (m, 1H), 1.67-1.70 (m, 1H), 1.39 (br s, 9H).

Workup

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

Sources & evidence

ORD record
ord-b9cf345a965a4bd1b9076017ce4fde5a
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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