Potassium Carbonate → (3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methanol

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	(3-Bromopyridin-4-yl)methanol	HCID 46840038	—
Reactant	1-(Propan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 56776710	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Product	(3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methanol	HCID 86690756	43.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a mixture of (3-bromopyridin-4-yl)methanol (150 mg, 0.8 mmol, 1 eq.), 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (226 mg, 0.96 mmol, 1.2 eq.), Pd(dppf)Cl2 (58 mg, 0.08 mmol, 0.1 eq.), and K2CO3 (331 mg, 3.0 mmol, 3 eq.) in a RB flask were added dioxane (6 mL) and water (2 mL). The mixture was heated at 100° C. for 2 h, cooled, filtered, and concentrated. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methanol (75 mg, 43%) as a yellow oil. LRMS (M+H+) m/z 218.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09012450B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-bc0aaf9afc144d0c9d82e70c4ac50ce0
Source note	uspto-grants-2015_04