Sodium Carbonate → HCID 90031248, 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 90064795	HCID 90064795	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol toluene water	HCID 86587398	—
Product	HCID 90031248	HCID 90031248	82.6%

Reaction Steps

Using similar reaction conditions as described in step-i of example-1, tert-butyl 4-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)piperazine-1-carboxylate (Intermediate 66N) (465 mg, 0.7 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (234 mg, 0.77 mmol) using sodium carbonate (223 mg, 21 mmol) and Pd(dppf)Cl2 (26 mg, 0.035 mmol) in toluene/ethanol/water (6/6/2 mL) to afford 410 mg (82.1% yield) of the titled compound after purification by column (Silica gel 60/120) using 30% ethyl acetate in hexane as eluent. MS: m/z=709.3 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-4f3225c3a3064b948ae9bd0e05af648e
Source note	uspto-grants-2016_05