N-methyl-2-pyrrolidone → HCID 69155969, compound

HRID 750150Notes

Reaction equation

HRID 750150 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].[CH3:33][N:34]1CCCC1=O>[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.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:33]#[N:34])=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 10239063HCID 10239063, compound

Product 1

HCID 69155969HCID 69155969, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), zinc cyanide (50 mg), tetrakis(triphenylphosphine)palladium(0) (35 mg) and 1-methyl-2-pyrrolidone (3 ml) was stirred at 100° C. for 2 hrs. under an argon atmosphere. Water was added to the reaction mixture, and the mixture was extracted with a mixture of ethyl acetate and THF. The organic layer was washed with aqueous ammonia, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure, and the obtained crystals were washed with a mixture of ethyl acetate and diethyl ether to give the title compound (210 mg).

Workup

  1. extractionthe mixture was extracted with a mixture of ethyl acetate and THF
  2. washThe organic layer was washed with aqueous ammonia, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)
  6. customThe solvent was evaporated under reduced pressure
  7. washthe obtained crystals were washed with a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-9a1839bc5c5a40d288339afda773b024
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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