4-Chloroquinoline → 7-Bromo-4-quinolin-4-yl-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241163

반응식

HRID 241163 반응식
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][NH:9][CH2:8][C:7]=2[CH:13]=1.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C>C(O)CCC.C(OCC)(=O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][N:9]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[CH:17][CH:16]=3)[CH2:8][C:7]=2[CH:13]=1

참가 물질

6

반응물 3

HCID 691404-ChloroquinolineHCID 81531DiisopropylethylamineHCID 668201377-Bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride

생성물 1

HCID 668207827-Bromo-4-quinolin-4-yl-2,3,4,5-tetrahydro-1,4-benzoxazepine수율 84.6%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (1.50 g, 5.67 mmol) (example 2, step 1), 4-chloroquinoline (0.973 g, 5.95 mmol), diisopropylethylamine (2.93 g, 22.7 mmol) in 1-butanol (15 mL) was stirred at 170° C. for 1 hour in a microwave synthesizer. The reaction mixture was diluted with ethyl acetate (100 mL), washed with saturated sodium bicarbonate (50 mL) and brine (50 mL), dried over sodium sulfate. Filtration and concentration afforded a crude brown oil that was purified by silica gel chromatography (9:1 dichloromethane/methanol) to provide 7-bromo-4-quinolin-4-yl-2,3,4,5-tetrahydro-1,4-benzoxazepine (1.70 g, 84.6% yield) as a yellow oil. MS (EI) for C18H15BrN2O: 356 (MH+).

후처리

  1. washwashed with saturated sodium bicarbonate (50 mL) and brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration and concentration
  4. customafforded a crude brown oil that
  5. customwas purified by silica gel chromatography (9:1 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-d7389744bcd647fc8245228d7df8eec0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648066B2

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