2,2'-Bipyridine → 2-Trifluoromethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	2,2'-Bipyridine	HCID 1474	—
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	(Trifluoromethyl)trimethylsilane	HCID 552549	—
Reactant	[Ethoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]acetic acid ethyl ester	HCID 66934051	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	2-Trifluoromethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester	HCID 68475847	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A solution of the product from step a.) (75 mg, 0.21 mmol) in DMF (0.5 ml) and NMP (0.5 ml) was treated with bipyridyl (43 mg, 0.27 mmol), CuI (44 mg, 0.23 mmol), KF (13 mg, 0.23 mmol) and trimethylsilyltrifluoromethane (2.1 ml, 1.05 mmol). The reaction mixture was heated to 80° C. for 3 days. The reaction was cooled and filtered through celite washing with EtOAc (20 ml). The eluent was washed with brine (2×3 ml) and dried (MgSO4) providing the subtitle compound as a brown oil that was used without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07718647B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-2bdb7c26d0cb4058bb29788725dfe7de
Source note	uspto-grants-2010_05