Sodium Carbonate → HCID 118524021, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 69132726	—
Reactant	HCID 90064796	HCID 90064796	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol toluene water	HCID 86587398	—
Product	HCID 118524021	HCID 118524021	70%

Reaction Steps

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)piperazine-1-carboxylate (Intermediate 66S) (175 mg, 0.254 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (115 mg, 0.380 mmol) using sodium carbonate (81 mg, 0.764 mmol) and Pd(dppf)Cl2 (9.4 mg, 0.012 mmol) in toluene/ethanol/water (20/10/4 mL) to afford 131 mg (70% yield) of the titled compound after purification by column (Silica gel 60/120) using 37% ethyl acetate in hexane as eluent.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-7748f15e91144c7e8ffc3e441fdebfac
Source note	uspto-grants-2016_05