Trimethylsilylacetylene → 6-(4-chlorobenzoyl)-1-methyl-4-(3-((trimethylsilyl)ethynyl)phenyl)-1,8-naphthyridin-2(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	4-(3-bromophenyl)-6-(4-chlorobenzoyl)-1-methyl-1,8-naphthyridin-2(1H)-one	HCID 70882515	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	6-(4-chlorobenzoyl)-1-methyl-4-(3-((trimethylsilyl)ethynyl)phenyl)-1,8-naphthyridin-2(1H)-one	HCID 67428830	80%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of compound I (1 g, 2.21 mmol) in THF (10.0 mL), TEA (4 mL) was added followed by (PPh3)4Pd (0.25 g, 0.22 mmol) and CuI (42 mg, 0.22 mmol). The mixture was degassed using N2 for 30 min and TMS-acetylene (0.92 g, 6.64 mmol) was added. The mixture was heated in a microwave oven at 60° C. for 30 min. The reaction mixture was diluted with EtOAc (25 mL) and passed through a pad of celite. The filtrate was concentrated. Purification of the crude product provided 825 mg (80%) of compound J.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08343996B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-bfc77b2325be41759c33360caf200a9f
Source note	uspto-grants-2013_01