Boron Trichloride → (3S)-3-ethyl-7-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898267ノート

反応式

HRID 898267 の反応式
[CH2:1]([C@@H:3]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:11]2[C:6](=[CH:7][C:8]([F:24])=[CH:9][CH:10]=2)[N:5]([CH3:25])[C:4]1=[O:26])[CH3:2].B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:1]([C@@H:3]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)(=[O:14])=[O:15])[C:11]2[C:6](=[CH:7][C:8]([F:24])=[CH:9][CH:10]=2)[N:5]([CH3:25])[C:4]1=[O:26])[CH3:2]

参加物

5

反応物 2

HCID 25135Boron TrichlorideHCID 69220473(3S)-3-ethyl-7-fluoro-4-[(4-methoxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

生成物 1

HCID 11639171(3S)-3-ethyl-7-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one収率 78.4%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of (3S)-3-ethyl-7-fluoro-4-[(4-methoxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one (0.27 g, 0.7 mmol)) and tetrabutylamonium iodide (0.77 g, 2.09 mmol) in methylene chloride (20 mL) was cooled to −78° C. and treated with a 1M solution of boron trichloride in methylene chloride (3.5 mL, 3.5 mmol) via syringe. The cooling bath was removed and the solution was stirred at 25° C. for 3 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride. The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo. The crude oil was purified via flash column chromatography (SiO2, 40% ethyl acetate:hexane) to afford 0.2 g (78%) of (3S)-3-ethyl-7-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one as white solid. MS (ESI) m/z 365 ([M+H]+); MS (ESI) m/z 363 ([M−H]−); Anal. Calcd for C17H17FN2O4S: C, 56.03; H, 4.70; N, 7.69. Found: C, 56.12; H, 4.03; N, 7.45.

後処理

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude oil was purified via flash column chromatography (SiO2, 40% ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-d5f8b475495a46bab4eedc65bc1e5b34
出典データセット
uspto-grants-2008_04
特許番号
US07351709B2

反応ノート

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