4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 6-(1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine

Participants

Role	Name	HCID	Charge
Reactant	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 2774010	—
Reactant	2-[(6-Chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silane	HCID 86707030	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Sodium Carbonate	HCID 10340	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-(1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine	HCID 86707161	46.2%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A suspension of 6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine (1.30 g, 4.6 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.16 g, 6 mmol), and Pd(dppf)Cl2 (437 mg, 0.6 mmol) in aq. Na2CO3 (2.0 M, 12 mL) and 1,4-dioxane (20 mL) was heated at 110° C. for 20 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography using ethyl acetate/heptanes 50% to 100% as eluting solvents to afford 6-(1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine as a yellow oil (670 mg, 46%), and recovered 1 g of the starting material. MS (ESI) m/z: 316 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434725B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-d08bd09121604b0c84895928fcefa6cc
Source note	uspto-grants-2016_09