Dichloromethane → HCID 10386099、化合物

反応式

[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]

参加物

反応物 4

HCID 6344Dichloromethane

HCID 8079Cyclohexene

HCID 25134Boron tribromide

HCID 22482290HCID 22482290、化合物

生成物 1

HCID 10386099HCID 10386099、化合物収率 60.7%

実験手順

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.;

後処理

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×)

出典と根拠

ORDレコード: ord-636c280bc99041d9b458952790d1cf09
出典データセット: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06894061B2

反応ノート

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