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

HRID 1509323노트

반응식

HRID 1509323 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-61c0b0cbab7e41c791341c5d515ea3fb
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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