Triethylamine → Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	Benzoic acid, 4-amino-2-chloro-5-iodo-, methyl ester	HCID 11839203	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate	HCID 59625799	—

Reaction Steps

To a mixture of compound 22k (200 mg, 0.642 mmol), CuI (12.2 mg, 0.064 mmol) and Pd(PPh3)2Cl2 (45 mg, 0.064 mmol) in THF (2 mL) was added ethynyltrimethylsilane (95 mg, 0.963 mmol) followed by Et3N (1 mL, 7.19 mmol) under N2. The reaction mixture was stirred at room temperature for 1.5 h and then partitioned between EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 22m.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748417B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-319cae63c22f4f94b49f24cd31a794ed
Source note	uspto-grants-2014_06