Dichloromethane → 3-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181853노트

반응식

HRID 2181853 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:27].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH:5]2[CH3:27]

참가 물질

5

반응물 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224822658-Fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

생성물 1

HCID 99763533-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol수율 77%

실험 절차

The title compound was prepared from 8-fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.50 g, 1.3 mmol), cyclohexene (2.4 mL, 24 mmol), and 1 M boron tribromide in dichloromethane (7.8 mL, 7.8 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 trituration from hexane, to yield 3-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.37 g, 71%), m.p. 161° C.;

후처리

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

출처 및 근거

ORD 기록
ord-847732f1ef5c41d18951a69d66792943
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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