Dimethylformamide → HCID 66772244, compound

HRID 1645260

Reaction equation

HRID 1645260 reaction equation
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]

Participants

9

Reactant 6

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

Product 1

HCID 66772244HCID 66772244, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-dfff84b0d0214ac1b9cce94e054bf1f8
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Linked notes

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