Potassium Phosphate, Tribasic → HCID 90030845, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Tricyclohexylphosphine	HCID 75806	—
Reactant	tert-butyl 4-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate	HCID 90031152	—
Reactant	5-bromo-3-(1-phenethyl-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 90064825	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	HCID 90030845	HCID 90030845	57.2%

Reaction Steps

Using similar reaction conditions as described in step-i of example-1, 5-bromo-3-(1-phenethyl-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (intermediate 63A) (160 mg, 0.307 mmol) was coupled with tert-butyl 4-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (intermediate 70) (307 mg, 0.769 mmol) using potassium phosphate (195 mg, 0.918 mmol), tricyclohexyl phosphine (13 mg, 0.046 mmol) and Pd2(dba)3 (28 mg, 0.030 mmol) in dioxane/water (15/3 ml) to afford 126 mg (57.2% yield) of the pure product after column purification using 35% ethyl acetate in hexane as eluent. MS: m/z=718.3 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-fb8ef6a4464245c085d7f98023ae842d
Source note	uspto-grants-2016_05