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

HRID 898267노트

반응식

HRID 898267 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6344Dichloromethane용매2회

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온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d5f8b475495a46bab4eedc65bc1e5b34
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07351709B2

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