Tributyltin fluoride → Methyl[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate

Participants

Role	Name	HCID	Charge
Reactant	Tributyltin fluoride	HCID 16120	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	1-(Tert-butyldimethylsilyloxy)-1-methoxyethane	HCID 23077686	—
Reactant	3-Benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide	HCID 58859131	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Toluene	HCID 1140	—
Product	Methyl[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate	HCID 58859124	62.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 3-benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (300 mg) obtained in Example 161, Step 2 in toluene were added under an argon stream tributyltin fluoride (518 mg), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (58 mg), 1,1′-bis(diphenylphosphino)ferrocene (64 mg) and 1-(tert-butyldimethylsilyloxy)-1-methoxyethane (525 mg), and the mixture was stirred at 100° C. for 15 hr. After cooling to room temperature, aqueous sodium hydrogen carbonate was added to the reaction mixture and the mixture was extracted three times with ethyl acetate. The extract was dried, concentrated and purified by silica gel column chromatography (ethyl acetate) to give methyl [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate (184 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07211572B2
Source dataset	uspto-grants-2007_05
ORD ID	ord-86457739ccdb438694853baaa7b6936c
Source note	uspto-grants-2007_05