Triethylamine → 5-Nitro-3-trimethylsilanylethynyl-1-trityl-1H-indazole

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	3-bromo-5-nitro-1-trityl-1H-indazole	HCID 58946443	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-Nitro-3-trimethylsilanylethynyl-1-trityl-1H-indazole	HCID 57685863	67.8%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 3-bromo-5-nitro-1-trityl-1H-indazole (4.83 g, 10 mmol), ethynyl-trimethyl-silane (1 g, 10 mmol), copper (I) iodide (91 mg, 0.5 mmol), PdCl2(dppf) (337 mg, 0.5 mmol) and triethylamine (1.2 g, 12 mmol) in DMF (50 mL) was stirred overnight at 80° C. under argon. Then ethyl acetate (100 mL) was added, followed by water. The organic layer was collected and aqueous layer was extracted three times with ethyl acetate. The combined organic fraction was washed with water and then brine. The solvent was removed under vacuum and the product was purified using chromatography (20% hexane in dichloromethane) to give desired product (3.4 g) in 67% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546404B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-4e5b70f7ff1e4816a8379f21f48a784c
Source note	uspto-grants-2013_10