Triethylamine → 5-(1-Benzyl-5-iodo-1h-1,2,3-triazol-4-yl)-2-fluorobenzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Benzyl azide	HCID 12152	—
Reactant	Iodine chloride	HCID 24640	—
Reactant	5-Ethynyl-2-fluorobenzonitrile	HCID 53429295	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	5-(1-Benzyl-5-iodo-1h-1,2,3-triazol-4-yl)-2-fluorobenzonitrile	HCID 68737269	—

Reaction Steps

A mixture of Example 62B (200 mg, 1.38 mmol), benzyl azide (0.176 mL, 1.38 mmol), tetrahydrofuran (12 mL), triethylamine (0.230, 1.56 mmol), CuI (263 mg, 1.38 mmol) and ICl (0.069 mL, 1.38 mmol) under argon was stirred at room temperature for 24 hours. The solvent was evaporated and the crude mixture was dissolved in dichloromethane, loaded directly onto a silica gel column and eluted with ethyl acetate/hexanes (10-20%) to afford the title compound. MS (ESI+) m/z 404.9 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08648069B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-b00cfb69ab754b22a80396f628cb1697
Source note	uspto-grants-2014_02