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

HRID 2181849노트

반응식

HRID 2181849 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]([Cl:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2].B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:29][C:23]1[CH:22]=[C:21]([S:18]([N:4]2[CH:3]([CH2:1][CH3:2])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=3)[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)(=[O:19])=[O:20])[CH:26]=[CH:25][C:24]=1[OH:27]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 22482342HCID 22482342, 화합물

생성물 1

HCID 99793892-chloro-4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol수율 41%

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide촉매

실험 절차

The title compound was prepared from 6-ethyl-8-fluoro-5-[(3-chloro-4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.41 g, 0.96 mmol), tetrabutylammonium iodide (0.85 g, 2.3 mmol), and 1 M boron trichloride in dichloromethane (6.7 mL, 6.7 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 (20:80 to 35:65 gradient), followed by re-crystallization from a mixture of ethyl acetate-hexane, to yield 2-chloro-4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.16 g, 41%), m.p. 174-177° C.;

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (20:80 to 35:65 gradient)
  3. customfollowed by re-crystallization from a mixture of ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-7085b43db0144f709e81e423c66ba17a
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

반응 노트

불러오는 중…