Ethanol → HCID 57526918, compound

HRID 2261023Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:9]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:10](=[O:22])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[C:30]([O-:33])(=[O:32])C.[Na+].[CH2:35](O)[CH3:36]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:35]([O:33][C:30]([C:2]1[CH:7]=[C:6]([C:8]2[N:9]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:10](=[O:22])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])[CH:12]=2)[CH:5]=[CH:4][N:3]=1)=[O:32])[CH3:36]

Participants

Conditions

Temperature: 80 °C

Procedure

In 20 ml of ethanol were suspended 1 g of 4-(2-chloropyridin-4-yl)-3-(4-fluorophenyl)-1-(2-cyanobenzyl)-4-imidazolin-2-one [Compound of Reference example 1(6)], 55 mg of palladium acetate, 137 mg of 1,1′-bis(diphenylphosphino)ferrocene and 608 mg of sodium acetate, the mixture was stirred under carbon monoxide atmosphere at 80° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, the residue was suspended in ethyl acetate, treated with activated charcoal and then filtered. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2) to give 887 mg of the title compound as colorless crystal. Melting point: 164° C.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additiontreated with activated charcoal
filtrationfiltered
concentrationAfter concentration under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record: ord-8fd9dbc2245243368f885d26c9e6c553
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846933B2

Reaction notes

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