Dimethylformamide → 4-(5-Methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrile

HRID 717091Notes

Reaction equation

HRID 717091 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:19])[C:11]3[C:16]([CH:17]=2)=[C:15]([CH3:18])[CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[CH3:20][N:21](C=O)C>[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>[CH3:18][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH:17]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:20]#[N:21])=[CH:3][CH:4]=1)[NH:9][C:10]2=[O:19]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 762845543-(4-Bromophenyl)-5-methyl-1(2h)-isoquinolinone

Product 1

HCID 898129544-(5-Methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrileYield 79%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-(4-Bromo-phenyl)-5-methyl-2H-isoquinolin-1-one (200 mg, 0.64 mmol), zinc cyanide (90 mg, 0.76 mmol) and tetrakis(triphenylphosphine)palladium(0) (74 mg, 0.064 mmol) were stirred in DMF (2.1 mL) and degassed with N2. The reaction mixtures were irradiated using a microwave (300 W, 180° C., 30 min). The reaction mixtures were combined and the resulting precipitate was filtered, washed with DMF and water and dried to give 4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrile as a yellowish solid (718 mg, 79%) which was used in the next step without further purification.

Workup

  1. customdegassed with N2
  2. customThe reaction mixtures
  3. customwere irradiated
  4. customa microwave (300 W, 180° C., 30 min)
  5. customThe reaction mixtures
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with DMF and water
  8. customdried

Sources & evidence

ORD record
ord-e1c5511e683f41ea9684beca2c6ba8ea
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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