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

HRID 2036692Notes

Reaction equation

HRID 2036692 reaction equation
[F: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]=[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>>[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 23717246Sodium 3-fluorobenzene-1-sulfinateHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085414Tert-butyl 2-(3-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 46%

Procedure

Intermediate 2 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, hexanes/ethyl acetate) to give tert-butyl 2-(3-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (110 mg, 46%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.13-8.23 (m, 1H), 7.71-7.76 (m, 1H), 7.58-7.70 (m, 2H), 7.38-7.49 (m, 1H), 7.28-7.35 (m, 1H), 7.12-7.23 (m, 1H), 5.16-5.38 (m, 1H), 4.32-4.51 (m, 1H), 3.60 (s, 3H), 3.20-3.50 (m, 1H), 2.50 (d, J=16.2 Hz, 1H), 2.10-2.40 (m, 2H), 1.85-1.98 (m, 1H), 1.56-1.68 (m, 1H), 1.37 (br s, 9H).

Workup

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

Sources & evidence

ORD record
ord-75358a6f99af4975a3816d8cdfa4435f
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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