Cesium fluoride → 6'-Methyl-2,3'-bipyridine-2'-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Cesium fluoride	HCID 25953	—
Reactant	2-(Tributylstannyl)pyridine	HCID 607784	—
Reactant	3-Bromo-6-methylpyridine-2-carbonitrile	HCID 21952747	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Dimethylformamide	HCID 6228	—
Product	6'-Methyl-2,3'-bipyridine-2'-carbonitrile	HCID 59363716	88%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 3-bromo-6-methylpicolinonitrile (1 g, 5.1 mmol), 2-(tributylstannyl)pyridine (2.43 ml, 6.60 mmol), cesium fluoride (150 mg, 10.2 mmol), CuI (193 mg, 1.02 mmol) and Pd(PPh3)4 (586 mg, 0.51 mmol) in DMF (10 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a brown oil (0.87 g, 88%). MS (ESI) 196 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440982B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-ca8ed7fd06cf4ff3a8a7b5ac5854dc1b
Source note	uspto-grants-2016_09