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

HRID 1509320노트

반응식

HRID 1509320 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.[F:19][CH2:20][CH2:21]I.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]([CH2:21][CH2:20][F:19])[C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

생성물 1

HCID 866836766-bromo-1-(2-fluoroethyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one수율 45.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (400 mg, 1.311 mmol), 1-fluoro-2-iodoethane (684 mg, 3.93 mmol) and potassium carbonate (544 mg, 3.93 mmol) in DMF (4 ml) was heated under stirring for 3 h. The reaction mixture was cooled down and diluted with water (20 ml), the resulted mixture was extracted with DCM (3×20 ml). The combined organic phase was washed with water, brine, dried over sodium sulfate, concentrated to give the crude material which was purified by column chromatography eluted with ethyl acetate/cyclohexane 0-40% to give product 0.21 g. 1H NMR (500 MHz, CDCl3): 7.39-7.48 (m, 5H), 4.89 (s, 2H), 4.77 (t, 1H), 4.67 (t, 1H), 4.21 (t, 1H), 4.16 (t, 1H), LCMS (Method D): RT=1.24 min, M+H+=353.0.

후처리

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled down
  3. extractionthe resulted mixture was extracted with DCM (3×20 ml)
  4. washThe combined organic phase was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give the crude material which
  8. customwas purified by column chromatography
  9. washeluted with ethyl acetate/cyclohexane 0-40%

출처 및 근거

ORD 기록
ord-433e6dee90dd4c76abe72896eaa60e97
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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