3-(Trifluoromethoxy)benzenesulfinic acid sodium salt → Tert-butyl 2-(3-trifluoromethoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036699Notes

Reaction equation

HRID 2036699 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([S:10]([O-:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[Na+].Br[C:17]1[CH:25]=[CH:24][C:23]2[N:22]([CH3:26])[C:21]3[CH2:27][CH:28]4[NH:32][CH:31]([C:20]=3[C:19]=2[C:18]=1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][CH2:29]4>>[F:14][C:2]([F:1])([F:13])[O:3][C:4]1[CH:5]=[C:6]([S:10]([C:17]2[CH:25]=[CH:24][C:23]3[N:22]([CH3:26])[C:21]4[CH2:27][CH:28]5[NH:32][CH:31]([C:20]=4[C:19]=3[C:18]=2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][CH2:29]5)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 509987763-(Trifluoromethoxy)benzenesulfinic acid sodium saltHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085643Tert-butyl 2-(3-trifluoromethoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylateYield 32%

Procedure

Intermediate 3 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, 7:3 hexane/ethyl acetate) to give tert-butyl 2-(3-trifluoromethoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (110 mg, 32%) as an off-white solid: 1H NMR (CDCl3, 300 MHz): δ 8.18 (s, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.81 (s, 1H), 7.67 (dd, J=8.6, 1.4 Hz, 1H), 7.50 (t, J=8.1 Hz, 1H), 7.29-7.38 (m, 2H), 5.13-5.40 (m, 1H), 4.49-4.84 (m, 1H), 3.61 (s, 3H), 3.20-3.52 (m, 1H), 2.50 (d, J=16.2 Hz, 1H), 2.12-2.41 (m, 2H), 1.86-2.00 (m, 1H), 1.58-1.68 (m, 1H), 1.37 (br s, 9H).

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-440d6508b2274fd585a5cd6356cbf03d
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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