Water → 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinoline

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 2773987	—
Reactant	5-Bromo-6-methoxyquinoline	HCID 18414128	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinoline	HCID 68902011	139.3%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 5-bromo-6-methoxy-quinoline (6.5 g, 0.021 mol), 1-methyl-4-pyrazoleboronic acid pinacol ester (8.74 g, 0.042 mol), Na2CO3 (6.687 g, 0.063 mol), Pd(dppf)Cl2 (1.7 g, 0.001 mol), H2O (32 mL) and 1,4-dioxane (80 mL) was heated at 100° C. overnight. After cooling down to room temperature, most of the dioxane was removed under vacuo. The mixture was diluted with ethyl acetate (50 mL) and brine (50 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give compound 7 g of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinoline.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08507489B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-7a8e3d7d31174730aec02b644aae89f3
Source note	uspto-grants-2013_08