Methanol → 1,2-Dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile

HRID 2293467Notes

Reaction equation

CN([CH:4]=[C:5]([C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=O)C.[C:23]([CH2:25][C:26]([NH2:28])=[O:27])#[N:24].CO.[H-].[Na+]>CN(C=O)C>[F:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[NH:28][C:26](=[O:27])[C:25]([C:23]#[N:24])=[CH:4][C:5]=2[C:15]2[CH:16]=[CH:17][C:18]([S:21][CH3:22])=[CH:19][CH:20]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 26.1 g of 1-(N,N-dimethylamino)-3-(4-fluorophenyl)-2-[4-(methylthio)phenyl]prop-1-en-3-one (Step 1), 200 ml of dry DMF, 7.2 g (8.6 mMol) of the cyanoacetamide and 8 ml methanol was transferred to a dropping funnel. This solution was added dropwise to a slurry of 4.0 g of sodium hydride in 100 ml of DMF in a 3-necked round bottom flask with a magnetic stirrer and cooled with an ice bath. The temperature reached to 25° C. After complete addition of the reactants the mixture was heated to 80° C. for 4 hours, cooled and poured into one liter of 1M NaH2PO4 to give an insoluble yellow solid which was washed with water and air dried to yield 24.5 g of a yellow powder (95%).

Workup

temperaturecooled with an ice bath
customreached to 25° C
additionAfter complete addition of the reactants the mixture
temperaturecooled
customto give an insoluble yellow solid which
washwas washed with water and air
customdried

Sources & evidence

ORD record: ord-e9b81fb63f0646769a70bc990e7e492b
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686470

Reaction notes

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