Sodium 4-chlorobenzenesulfinate → HCID 67085117, compound

HRID 2036713Notes

Reaction equation

HRID 2036713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].Br[C:13]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3[CH2:23][CH:24]4[NH:28][CH:27]([C:16]=3[C:15]=2[C:14]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]4>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]5)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 23664783Sodium 4-chlorobenzenesulfinateHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085117HCID 67085117, compoundYield 40%

Procedure

Intermediate 18 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, 3:2 hexanes/ethyl acetate) to give tert-butyl 2-(4-chlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (100 mg, 40%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.16 (s, 1H), 7.86-7.90 (m, 2H), 7.62-7.66 (m, 1H), 7.43-7.45 (m, 1H), 7.32-7.42 (m, 1H), 7.29-7.32 (m, 1H), 5.25 (br s, 1H), 4.68 (br s, 1H), 4.70 (s, 1H), 3.60 (s, 3H), 2.50 (d, J=16.3 Hz, 1H), 2.17-2.33 (m, 2H), 1.89-1.97 (m, 1H), 1.55-1.65 (m, 1H), 1.37 (br s, 9H).

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 3:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-57017fc4386c4ca5bfeb472bb18d3a97
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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