Sodium 4-methoxybenzene-1-sulfinate → Tert-butyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036687노트

반응식

HRID 2036687 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[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>>[CH3:1][O:2][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

참가 물질

3

반응물 2

HCID 23680956Sodium 4-methoxybenzene-1-sulfinateHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

생성물 1

HCID 67085572Tert-butyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate수율 34%

실험 절차

Intermediate 14 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 (8:2 hexanes/ethyl acetate) to give tert-butyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (106 mg, 34%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.17 (s, 1H), 7.88 (d, J=8.7 Hz, 2H), 7.60-7.71 (m, 1H), 7.27-7.32 (m, 1H), 6.92 (d, J=9.0 Hz, 2H), 5.26 (br s, 1H), 4.69 (br s, 1H), 3.82 (s, 3H), 3.59 (s, 3H), 3.40 (br s, 1H), 2.49 (d, J=16.2 Hz, 1H), 2.12-2.39 (m, 2H), 1.88-2.01 (m, 1H), 1.53-1.72 (m, 1H), 1.38 (br s, 9H).

후처리

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

출처 및 근거

ORD 기록
ord-3f998e53c5224ffb99c2b5aabbab3952
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575186B2

반응 노트

불러오는 중…