Dichloromethane → HCID 10386099, 화합물

HRID 2181859노트

반응식

[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[C:8]([CH3:18])[CH:7]=[CH:6][C:5]=2[N:4]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH3:2].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[C:8]([CH3:18])[CH:7]=[CH:6][C:5]=2[N:4]1[S:19]([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)(=[O:21])=[O:20])[CH3:2]

참가 물질

반응물 4

HCID 6344Dichloromethane

HCID 8079Cyclohexene

HCID 25134Boron tribromide

HCID 22482290HCID 22482290, 화합물

생성물 1

HCID 10386099HCID 10386099, 화합물수율 60.7%

실험 절차

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-methyl-5,6-dihydrophenanthridine (0.24 g, 0.58 mmol), cyclohexene (2.1 mL, 21 mmol), and 1 M boron tribromide in dichloromethane (7.0 mL, 7.0 mmol) according to the procedure and in the same manner as described in Example 47, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4), followed by re-crystallization from a mixture of ethyl acetate-hexane (2×), to afford 4-[(6-ethyl-8-fluoro-2-methylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.14 g, 59%), m.p. 197-200° C.;

후처리

customThe crude product was purified by flash column chromatography on silica gel
washeluting with a mixture of ethyl acetate-hexane (1:4)
customfollowed by re-crystallization from a mixture of ethyl acetate-hexane (2×)

출처 및 근거

ORD 기록: ord-636c280bc99041d9b458952790d1cf09
출처 데이터셋: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06894061B2

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