Water → Methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-Ethyl-1H-pyrazole-4-boronic acid, pinacol ester	HCID 11379045	—
Reactant	Methyl 2-chloro-4-cyanonicotinate	HCID 58317566	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate	HCID 58317527	114.4%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of methyl 2-chloro-4-cyanonicotinate (207 mg, 1.053 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (201 mg, 0.905 mmol) and tetrakis(triphenylphosphine)palladium(0) (122 mg, 0.105 mmol) in DME (2 mL), and saturated aq Na2CO3 (2 mL) was stirred at 80° C. for 3 h under N2 atmosphere. Water and EtOAc were subsequently added. The organic phase was washed with H2O and brine, dried over MgSO4, and evaporated to yield the title compound (265.3 mg, 98%). [M+H] calc'd for C13H12N4O2, 257. found, 257.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181255B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-c09a2223876342ccad63b242377912a8
Source note	uspto-grants-2015_11