2-Pyridone → 1-{3-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]prop-2-en-1-yl}pyridin-2(1H)-one

HRID 238296Notes

Reaction equation

HRID 238296 reaction equation
[H-].[Na+].[NH:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=[O:9].Cl[CH2:11][CH:12]=[CH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[N:18]=1>CN(C=O)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[N:18]=[C:14]([CH:13]=[CH:12][CH2:11][N:3]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]3=[O:9])[S:15][CH:16]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 88712-PyridoneHCID 24758Sodium hydrideHCID 688217062-(3-Chloroprop-1-en-1-yl)-4-(4-fluorophenyl)-1,3-thiazole

Product 1

HCID 688211721-{3-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]prop-2-en-1-yl}pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

23.7 mg (0.54 mmol) of sodium hydride (55% in mineral oil) were added to 60.4 mg (0.54 mmol) of 1H-pyridin-2-one in 8 ml of DMF. The mixture was stirred at room temperature for 1 h, 92 mg (0.36 mmol) of 2-(3-chloropropenyl)-4-(4-fluorophenyl)thiazole were added, and the mixture was stirred at room temperature for another 4 h and subsequently at 50° C. for 2 h. After concentrating, water was added and the product was extracted with ethyl acetate. The organic phases were evaporated and the residue was purified by preparative HPLC (RP18, acetonitrile/water containing 0.1% TFA). Yield: 26 mg (23%).

Workup

  1. stirringthe mixture was stirred at room temperature for another 4 h and subsequently at 50° C. for 2 h
  2. concentrationAfter concentrating
  3. additionwater was added
  4. extractionthe product was extracted with ethyl acetate
  5. customThe organic phases were evaporated
  6. customthe residue was purified by preparative HPLC (RP18, acetonitrile/water containing 0.1% TFA)

Sources & evidence

ORD record
ord-784574b885ec4fd7b9e7791964b7ad2e
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

Loading…