Triethylamine → 4-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	tert-Butyl 4-ethynylpiperidine-1-carboxylate	HCID 15550481	—
Reactant	6-Chloro-4-iodopyridin-3-ol	HCID 53302038	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester	HCID 86674889	—

Reaction Steps

Copper (I) iodide (25 mg) and bis-(triphenylphosphin)-palladium(II)-chloride (30 mg) are added to 6-chloro-4-iodo-pyridin-3-ol (200 mg) in N,N-dimethylformamide (3 mL) under an argon atmosphere. Triethylamine (110 μL) is added and the resulting mixture is stirred at room temperature for 1 h. A solution of 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (175 mg) in N,N-dimethylformamide (2 mL) is added dropwise and the reaction mixture is stirred at 55° C. for 3 h. The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30) to give the title compound. LC (method 2): tR=1.40 min; Mass spectrum (ESI+): m/z=337 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08669271B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-6b9f772031804918a9eedc895c035903
Source note	uspto-grants-2014_03