Triethylamine → 3-Bromo-6-chloro-4-methylpyridine-2-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilyl cyanide	HCID 82115	—
Reactant	5-Bromo-2-chloro-4-methylpyridine 1-oxide	HCID 86652346	—
Solvent	Acetonitrile	HCID 6342	—
Product	3-Bromo-6-chloro-4-methylpyridine-2-carbonitrile	HCID 86652347	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 5-bromo-2-chloro-4-methylpyridine 1-oxide (from step 1) (1.0 eq.) in acetonitrile (0.2 M) was added TMSCN (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100° C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-50% ethyl acetate in hexane to give 3-bromo-6-chloro-4-methylpicolinonitrile.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08466167B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-030d2a33d9084dc5a3e153b7e10c039a
Source note	uspto-grants-2013_06