Dimethylformamide → HCID 66772244, 화합물

HRID 1645260

반응식

HRID 1645260 반응식
O=P(Cl)(Cl)Cl.[CH3:6][N:7]([CH:9]=[O:10])C.[CH3:11][C:12]1[CH:16]=[CH:15][O:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].N1C2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][C:24]1=O.N1CCCCC1>CCO.O>[CH3:11][C:12]1[CH:16]=[CH:15][O:14][C:13]=1[CH:30]=[C:29]1[C:28]2[C:6](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:7][C:9]1=[O:10]

참가 물질

9

반응물 6

HCID 6228DimethylformamideHCID 8082PiperidineHCID 10340Sodium CarbonateHCID 135873-MethylfuranHCID 24813Phosphorus oxychlorideHCID 321710Oxindole

생성물 1

HCID 66772244HCID 66772244, 화합물수율 25.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

A solution of POCl3 (0.60 mL, 7.08 mmol) in DMF (0.65 mL, 8.431 mmol) was stirred at rt for 1 h. The reaction was cooled to 0° C. and added 3-methylfuran (490 mg, 5.97 mmol) dropwise. The mixture was stirred at 0 C for 1 h and at 40 C for additional 40 min. The reaction mixture was poured into H2O (25 mL), neutralized (Na2CO3), and extracted with EtOAc (25 mL×5). The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude material was heated at reflux with oxindole (800 mg, 6.02 mmol) and piperidine (0.60 mL, 8.08 mmol) in EtOH (5 mL) for 3 h. The resulting precipitate was collected by filtration to yield the desired 3-((3-methylfuran-2-yl)methylene)indolin-2-one (340 mg). LCMS (ES): m/z 226 [M+1]+.

후처리

  1. extractionextracted with EtOAc (25 mL×5)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. temperatureThe crude material was heated
  6. filtrationThe resulting precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-dfff84b0d0214ac1b9cce94e054bf1f8
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124649B2

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