Dimethylformamide → HCID 66788331, compound

HRID 1623543Notes

Reaction equation

HRID 1623543 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH3:13][N:14](C=O)C>C(=O)(O)[O-].[Na+].ClCCl.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:13]#[N:14])[CH:10]=2)[CH2:6][C:7]1=[O:12]

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 580060486-Bromo-1-methylindolin-2-one

Product 1

HCID 66788331HCID 66788331, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6-bromo-1-methyl-1,3-dihydro-indol-2-one (226 mg, 1.0 mmol) in DMF (6.0 mL) was added zinc cyanide (117 mg, 1.0 mmol). Then the reaction mixture was degassed and placed under an argon atmosphere and tetrakis(triphenylphosphine)palladium(0) (115 mg, 0.1 mmol) was added. The reaction was then placed at 95° C. for 100 minutes, at which time it was cooled to room temperature, and diluted with saturated aqueous sodium bicarbonate and dichloromethane. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 4%) to furnish 1-methyl-2-oxo-2,3-dihydro-1H-indole-6-carbonitrile; MS: (ES+) m/z 173.0 (M+H)+.

Workup

  1. customThen the reaction mixture was degassed
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted two additional times with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 4%)

Sources & evidence

ORD record
ord-ea81bf2640ad4ff0bba955d792fc8e03
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

Loading…