Sodium Carbonate → HCID 118524033, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}pyridine	HCID 17749926	—
Reactant	tert-butyl 4-(2-fluoro-4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate	HCID 90033965	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol toluene water	HCID 86587398	—
Product	HCID 118524033	HCID 118524033	—

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)phenyl)piperidine-1-carboxylate (Intermediate 67B) (150 mg, 0.52 mmol) was coupled with 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine (intermediate 64G) (180 mg, 0.63 mmol) using sodium carbonate (165 mg, 1.56 mmol) and Pd(dppf)Cl2 (18 mg, 0.026 mmol) in toluene/ethanol/water (10/10/2 mL) to afford 142 mg (crude) of the titled compound. MS: m/z=589.4 (M-Boc+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-12d014a821964508a001e4f2aa556a8a
Source note	uspto-grants-2016_05