Water → 2-((Trimethylsilyl)ethynyl)nicotinonitrile

https://huagongshe.com/reaction/1772012

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	2-Chloronicotinonitrile	HCID 81079	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Product	2-((Trimethylsilyl)ethynyl)nicotinonitrile	HCID 13411113	61.3%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of 2-chloronicotinonitrile (21.6 g, 156 mmol) in toluene (200 mL) was added Pd(dppf)Cl2 (2.3 g, 3.12 mmol), copper (I) iodide (594 mg, 3.12 mmol), triethylamine (32 mL, 312 mmol) and ethynyltrimethylsilane (23 g, 234 mmol). The reaction mixture was stirred at 70° C. under N2 for 5 h. The reaction mixture was filtered through a Celite pad. The filtrate was concentrated under reduced pressure to give a residue. 40 mL of water was added to the residue, and the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (1×100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluting with a gradient of PE/EtOAc v/v 40:1, 20:1, 10:1, 5:1) to yield 2-((trimethylsilyl)ethynyl)nicotinonitrile as a yellow solid (19.14 g, yield 61%). ESI MS: m/z 201 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249162B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-d883dcf8f6c84536b44d10a2a48d1a1e
Source note	uspto-grants-2016_02