Dichloromethane → HCID 66788680, compound

HRID 1623546Notes

Reaction equation

HRID 1623546 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:12])[N:6]2[CH3:11].P([O-])([O-])([O-])=[O:14].[K+].[K+].[K+].[CH:21]1([B-](F)(F)F)[CH2:23][CH2:22]1.[K+].ClCCl>C1COCC1.C(OCC)(=O)C.[Cl-].[Na+].O.O>[CH:21]1([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4](=[O:14])[C:5](=[O:12])[N:6]3[CH3:11])[CH2:23][CH2:22]1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 167379394-Bromo-1-methyl-1,3-dihydro-2H-indol-2-oneHCID 23697338Potassium cyclopropyltrifluoroborate

Product 1

HCID 66788680HCID 66788680, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 4-bromo-1-methyl-1,3-dihydro-indol-2-one, prepared in a fashion similar as described in Example 39a (CAS#884855-67-8, 1.80 g, 7.5 mmol) in THF (24 mL) was added water (8 mL), tripotassium phosphate (5.57 g, 26.3 mmol), and potassium cyclopropyltrifluoroborate (1.501 g, 10.50 mmol). The reaction mixture was degassed and placed under a nitrogen atmosphere, and then [1,1′-bis(diphenylphosphino)-ferrocene]-dichloropalladium(II) complexed with dichloromethane (CAS#72287-26-4 184 mg, 0.225 mmol) was added. The reaction vessel was sealed and was heated by microwave irradiation at 130° C. for 4 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate and brine and then filtered through a pad of Celite®. The layers of the filtrate were separated and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 100%) to furnish 4-cyclopropyl-1-methyl-1H-indole-2,3-dione; MS: (ES+) m/z 202.4 (M+H)+.

Workup

  1. customThe reaction mixture was degassed
  2. additionwas added
  3. customThe reaction vessel was sealed
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. filtrationfiltered through a pad of Celite®
  6. customThe layers of the filtrate were separated
  7. extractionthe aqueous layer was extracted two times with ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 100%)

Sources & evidence

ORD record
ord-f62272021ec84bcbb27e8228c296fd6d
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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