Potassium Carbonate → 6-bromo-7-phenyl-1-(2,2,2-trifluoroethyl)-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1509324노트

반응식

HRID 1509324 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.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]([F:30])([F:29])[CH2:27]I>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]([CH2:27][C:26]([F:30])([F:29])[F:25])[C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

생성물 1

HCID 866836786-bromo-7-phenyl-1-(2,2,2-trifluoroethyl)-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one수율 33.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °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), potassium carbonate (0.544 g, 3.93 mmol) and 1,1,1-trifluoro-2-iodoethane (0.826 g, 3.93 mmol) in DMF (2 ml) was heated at 70° C. under stirring for 18 h The reaction mixture was cooled down and diluted with water (15 ml) and extracted with DCM (15 mlX3). The combined organic phase was washed with water (25 ml) and dried with Na2SO4 and concentrated. The residue was purified by column chromatography (biotage 25 g) eluted with ethyl acetate/cyclohexane 0-60% to afford product 6-bromo-7-phenyl-1-(2,2,2-trifluoroethyl)-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (0.17 g) 1H NMR (500 MHz, CDCl3) 7.45-7.50 (m, 3H), 7.38-7.40 (m, 2H), 7.28 (s, 1H), 4.94 (s, 2H), 4.55 (q, 2H).

후처리

  1. temperaturewas cooled down
  2. extractionextracted with DCM (15 mlX3)
  3. washThe combined organic phase was washed with water (25 ml)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (biotage 25 g)
  7. washeluted with ethyl acetate/cyclohexane 0-60%

출처 및 근거

ORD 기록
ord-5acf97ac516640768613fb245a0e4829
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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