Dichloromethane → 6-(3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-b]pyridine

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	(3,5-Dimethoxyphenyl)boronic acid	HCID 4374257	—
Reactant	6-Bromo-1H-pyrazolo[4,3-b]pyridine	HCID 40152259	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-(3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-b]pyridine	HCID 86722862	82.7%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 6-bromo-1H-pyrazolo[4,3-b]pyridine (0.3 g, 2 mmol)(Annova Chem Cat. No. L05238), (3,5-dimethoxyphenyl)boronic acid (0.33 g, 1.8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (100 mg, 0.1 mmol), and potassium phosphate (0.64 g, 3.0 mmol) in 1,4-dioxane (1 mL) and water (0.12 mL) was degassed and sealed. It was stirred at 85° C. overnight. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.38 g). LCMS (M+H)+=256.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266892B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-fac0e585cac6421298c387341eb461bb
Source note	uspto-grants-2016_02