Ethyl Acetate → 4'-Fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	4-Fluorophenylboronic acid	HCID 285645	—
Reactant	N-(2-acetylamino-indan-5-yl)-2-bromo-benzamide	HCID 21253364	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	4'-Fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide	HCID 54376595	—

Reaction Steps

To a solution of N-(2-acetylamino-indan-5-yl)-2-bromo-benzamide (the title C compound; 0.150 g, 0.40 mmol) and 4-fluorobenzeneboronic acid (0.0.84 g, 0.60 mmol) in DME (7 mL) is added PdCl2(dppf) (0.010 g, 0.012 mmol) followed by K3PO4 (0.25 g, 1.20 mmol). The reaction mixture is degassed and heated at reflux under N2 atmosphere for 16 h. After cooling to room temperature, the reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give a tan solid. Trituration with ethyl acetate gives 4′-fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide as a grey solid, mp 218-220° C. MS (ES+), m/z 389 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06197798B1
Source dataset	uspto-grants-2001_03
ORD ID	ord-321e127da22f4698a5198e740bd6dc1a
Source note	uspto-grants-2001_03