Water → HCID 46830621, compound

HRID 1691796Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]([N:15]1[CH:20]=[CH:19][C:18](=[O:21])[CH2:17][CH:16]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:14].O.[CH3:29][N:30](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>[CH3:11][O:10][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]([C:29]#[N:30])=[C:3]([CH2:12][C:13](=[O:14])[N:15]2[CH:20]=[CH:19][C:18](=[O:21])[CH2:17][CH:16]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-[2-(2-Iodo-4,5-dimethoxy-phenyl)-acetyl]-2-phenyl-2,3-dihydro-1H-pyridin-4-one (269 mg, 0.56 mmol), zinc cyanide (1.5 eq, 99 mg) and tetrakis(triphenylphosphine)palladium(0) (0.15 eq, 98 mg) were dissolved in DMF. The mixture was heated to 80° C. overnight. Upon cooling, the mixture was poured into water and extracted with EtOAc. The organic extracts were dried over anhydrous sodium sulfate and concentrated en vacuo. The residue was purified by flash chromatography (7:3 Hexanes/Ethyl Acetate) to give 4,5-dimethoxy-2-[2-oxo-2-(4-oxo-2-phenyl-3,4-dihydro-2H-pyridin-1-yl)-ethyl]-benzonitrile (43 mg, 20.3%) viscous oil.

Workup

temperatureUpon cooling
extractionextracted with EtOAc
dry with materialThe organic extracts were dried over anhydrous sodium sulfate
concentrationconcentrated en vacuo
customThe residue was purified by flash chromatography (7:3 Hexanes/Ethyl Acetate)

Sources & evidence

ORD record: ord-285f02cb3d1b4d7db0bfad09ca99547f
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153808B2

Reaction notes

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