Dichloromethane → 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol

HRID 2181837노트

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HRID 2181837 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]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([CH3:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2].B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[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]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 22482394HCID 22482394, 화합물

생성물 1

HCID 100008734-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol수율 50%

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide촉매

실험 절차

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.53 g, 1.3 mmol), tetrabutylammonium iodide (1.2 g, 3.2 mmol), and 1 M boron trichloride in dichloromethane (8.9 mL, 8.9 mmol) according to the procedure and in the same manner as described in Example 35, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 1:1 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane to yield 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol as a homogeneous solid (0.25 g, 50%), m.p. 181° C.;

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:9 to 1:1 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

출처 및 근거

ORD 기록
ord-7507716b22c245998a7cefe0f1b35f2d
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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