HCID 11063780, compound → HCID 11030408, compound

HRID 2200159Notes

Reaction equation

HRID 2200159 reaction equation
[F:1][C:2]1(F)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][C:3]1=O>C1COCC1>[F:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][CH:3]=1

Participants

3

Reactant 1

HCID 11063780HCID 11063780, compound

Product 1

HCID 11030408HCID 11030408, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-tetrahydrofuran complex (1M, 15 mL) dropwise to the solution of 3,3-difluoro-5-nitroindolin-2-one (650 mg, 3 mmol) in THF (10 mL) at 0° C. After addition, stir the reaction at 70° C. for 5 hrs. Concentrate under reduced pressure, add ethyl acetate to the residue, wash the organic layer with saturated sodium bicarbonate solution twice and then with brine twice, dry over anhydrous sodium sulfate. Concentrate under reduced pressure to obtain the crude product. Purify by flash chromatography (silica gel, EtOAc:PE=1:3) to yield the title compound (500 mg, 91.5%).

Workup

  1. additionAfter addition
  2. customthe reaction at 70° C. for 5 hrs
  3. concentrationConcentrate under reduced pressure
  4. additionadd ethyl acetate to the residue
  5. washwash the organic layer with saturated sodium bicarbonate solution twice
  6. dry with materialwith brine twice, dry over anhydrous sodium sulfate
  7. concentrationConcentrate under reduced pressure
  8. customto obtain the crude product
  9. customPurify by flash chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-6acaf589071b406ebf2ec1ccaf42a530
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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