Potassium Carbonate → 2-(6-bromo-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)acetonitrile

HRID 1509323ノート

反応式

HRID 1509323 の反応式
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1.Br[CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[N:10]([CH2:20][C:21]#[N:22])[C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

生成物 1

HCID 866836792-(6-bromo-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)acetonitrile収率 42.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (0.4 g, 1.311 mmol), 2-bromoacetonitrile (0.472 g, 3.93 mmol) and potassium carbonate (0.544 g, 3.93 mmol) in DMF (4 ml) was stirred at 50° C. for 2 h. The reaction mixture was diluted with water (20 ml) and extracted with dichloromethane (3×20 ml). The combined organic phase was washed with water, brine, dried over sodium sulfate and concentrated to give crude product which was purified by column chromatography (biotage 25 g) eluted with 0-50% ethyl acetate/cyclohexane to afford product (0.19 g) 1H NMR (500 MHz, CDCl3) 7.45-7.50 (m, 3H), 7.4-7.43 (m, 2H), 7.31 (s, 1H), 4.93 (s, 2H), 4.83 (s, 2H).

後処理

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified by column chromatography (biotage 25 g)
  7. washeluted with 0-50% ethyl acetate/cyclohexane

出典と根拠

ORDレコード
ord-61c0b0cbab7e41c791341c5d515ea3fb
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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