Sodium Carbonate → HCID 90031001, 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 90031093	HCID 90031093	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol toluene water	HCID 86587398	—
Product	HCID 90031001	HCID 90031001	686.4%

Reaction Steps

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxyphenyl)piperazine-1-carboxylate (intermediate 52) (300 mg, 0.0435 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (145 mg, 0.479 mmol) using sodium carbonate (138 mg, 1.307 mmol) and Pd(dppf)Cl2 (16 mg, 0.0217 mmol) in toluene/ethanol/water (6/6/3 ml) to afford 220 mg (62.0% yield) of titled compound after purification by column (Silica gel 60/120) using 10% ethyl acetate in DCM as eluent. MS: m/z=737.2 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-8ffa44fc6652491a9e1a2ace375d4afb
Source note	uspto-grants-2016_05