Sodium 3-(difluoromethoxy)benzenesulfinate → Tert-butyl 2-(3-difluoromethoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

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Reaction Steps

Intermediate 6 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-difluoromethoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (155 mg, 43%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.12-8.22 (m, 1H), 7.76-7.82 (m, 1H), 7.62-7.72 (m, 2H), 7.46 (t, J=8.1 Hz, 1H), 7.32 (d, J=8.7 Hz, 1H), 7.21-7.26 (m, 1H), 6.52 (t, J=72.9 Hz, 1H), 5.19-5.38 (m, 1H), 4.55-4.80 (m, 1H), 3.61 (s, 3H), 3.20-3.51 (m, 1H), 2.50 (d, J=8.1 Hz, 1H), 2.12-2.40 (m, 2H), 1.89-1.99 (m, 1H), 1.55-1.67 (m, 1H), 1.37 (s, 9H).

Provenance & Evidence