Sodium Hydroxide → (3R)-N-[2'-(Hydroxymethyl)-1,1'-biphenyl-4-yl]-1-azabicyclo[2.2.2]octane-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	2-(Hydroxymethyl)phenylboronic Acid	HCID 4374262	—
Reactant	(3R)-N-(4-bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide	HCID 58742393	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(3R)-N-[2'-(Hydroxymethyl)-1,1'-biphenyl-4-yl]-1-azabicyclo[2.2.2]octane-3-carboxamide	HCID 58742401	—

Reaction Steps

A mixture of 90 mg (0.58 mmol) of 2-(hydroxymethyl)phenylboronic acid, 120 mg (0.39 mmol) of (3R)-N-(4-bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide, 1.16 ml (1.16 mmol) of 1N sodium hydroxide solution, 30 mg (0.04 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride and 1 ml of DMF is heated at 80–85° C. for 42 h. The solvent is removed under reduced pressure. The crude product is purified by chromatography on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol/ammonia 80:20:2). 56 mg (39% of theory) of the title compound are obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07138410B2
Source dataset	uspto-grants-2006_11
ORD ID	ord-7c93fa14db6b46c7a1f6e2cc09cd5912
Source note	uspto-grants-2006_11