Triethylamine → 5-Bromo-1-methyl-3-(2-trimethylsilylethynyl)pyridin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	HCID 117775552	HCID 117775552	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	5-Bromo-1-methyl-3-(2-trimethylsilylethynyl)pyridin-2-one	HCID 123767608	82.8%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 5-bromo-3-iodo-1-methylpyridin-2-one (8.0 g, 25.48 mmol), ethynyltrimethylsilane (2.7 g, 27.52 mmol), CuI (485 mg, 2.55 mmol), Pd(PPh3)2Cl2 (1.79 g, 2.55 mmol) and triethylamine (12.9 g, 127.4 mmol) in dry THF (100 mL) was heated to 60° C. under an atmosphere of nitrogen for 2 h. The mixture was concentrated and the residue was purified by column chromatography on silica gel (PE: EA=5:1) to give the title compound (6 g, 82%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ 7.61 (d, J=2.4 Hz, 1H), 7.42 (d, J=2.4 Hz, 1H), 3.54 (s, 3H), 0.25 (s, 9H). LCMS (M+H)+=285.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115114B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-92340a2a434d470494c3a0d9fc2089b2
Source note	uspto-grants-2015_08