Sodium Carbonate → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-[3-(1-pyrrolidinyl)phenyl]-1-benzofuran-2-carboxamide hydrochloride

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	1-(3-Bromophenyl)pyrrolidine	HCID 7016459	—
Reactant	N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride	HCID 67313982	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-[3-(1-pyrrolidinyl)phenyl]-1-benzofuran-2-carboxamide hydrochloride	HCID 67314003	—

Reaction Steps

114.3 mg (0.51 mmol) of 1-(3-bromophenyl)pyrrolidine, 148.1 mg (0.58 mmol) of bis(pinacolato)diboron, 124.1 mg (1.26 mmol) of potassium acetate, 14.2 mg (0.02 mmol) of PdCl2(dppf), 150 mg (0.39 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride (Example 30A), 0.97 ml of 2 M sodium carbonate solution and a further 14.2 mg (0.02 mmol) of PdCl2(dppf) in 2.0 ml of DMF are reacted by general method D. Drying under high vacuum results in 95.6 mg (54.4% of theory) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09067931B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-b451591c5ab74c2e8ec5835357995214
Source note	uspto-grants-2015_06