Nitrogen → 6-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Triethylamine	HCID 8471	—
Reactant	3,3-Dimethyl-1-butyne	HCID 13512	—
Reactant	6-Chloro-2-iodopyridin-3-amine	HCID 18407043	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	6-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine	HCID 57908159	88%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of 6-chloro-2-iodo-pyridin-3-ylamine (16.0 g, 62.7 mmol) in toluene (160 mL) and water (80 mL) were added Et3N (12.7 g, 125 mmol), Pd(PPh3)2Cl2 (2.2 g, 3.1 mmol), CuI (238 mg, 1.3 mmol) and 3,3-dimethyl-but-1-yne (7.7 g, 94 mmol) successively under N2 atmosphere. The reaction mixture was heated at 70° C. for 3 hours and was allowed to cool to room temperature. The resulting mixture was extracted with ethyl acetate (150 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give 6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine (11.5 g, 88%), which was used in the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08563573B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-1ce95d5be0f64daabb428b225b225bce
Source note	uspto-grants-2013_10