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

HRID 241163ノート

反応式

HRID 241163 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-d7389744bcd647fc8245228d7df8eec0
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

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