Methanol → 4-[(3-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol
反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:27])[N:13]([S:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=4)(=[O:18])=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C1CCCCC=1.B(Br)(Br)Br.CO>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:27])[N:13]([S:16]([C:19]4[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=4)(=[O:18])=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3参加物
反応条件
- 温度
- 0 °C
実験手順
To a stirred slurry of 3-fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (262 mg, 0.68 mmol) in cyclohexene (1.38 mL, 14 mmol) under an inert atmosphere of nitrogen was added a 1 M solution of boron tribromide in dichloromethane (4.1 mL). The progress of the reaction was monitored by thin-layered chromatography and after 2.5 hours the reaction was deemed complete. The reaction contents were cooled to 0° C. and methanol was added slowly. The volatile components were removed in vacuo and the crude residue was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 30%-50% methyl tert-butyl ether in hexane, to afford the title compound (77 mg, 30%) as a solid, m.p. 162-165° C.;
後処理
- customThe reaction contents
- customThe volatile components were removed in vacuo
- customthe crude residue was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
- washeluting with a gradient of 30%-50% methyl tert-butyl ether in hexane
出典と根拠
- ORDレコード
- ord-0264f9a5a647413785c1cee49df37f99
- 出典データセット
- uspto-grants-2005_05
- 特許番号
- US06894061B2
反応ノート
読み込み中…