Dimethylacetamide → 6-Amino-4-chloro-3-pyridinecarbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dimethylacetamide	HCID 31374	—
Reactant	2-Amino-5-bromo-4-chloropyridine	HCID 44181812	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Zinc	HCID 23994	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	6-Amino-4-chloro-3-pyridinecarbonitrile	HCID 21949219	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

5-bromo-4-chloropyridin-2-amine (500 mg, 2.41 mmol), zinc cyanide (297 mg, 2.53 mmol), zinc (31.5 mg, 0.482 mmol), Pd2(dba)3 (221 mg, 0.241 mmol), dppf (267 mg, 0.482 mmol) and DMA (20 ml) were charged into a flask under argon. The reaction mixture was stirred at 70° C. for 16 h. The reaction mixture was diluted in EtOAc and washed with sat. NaHCO3 (2×) and brine. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by normal phase chromatography (24 g silica gel cartridge, heptanes/EtOAc 100:0 to 58:42) to give the title compound as a beige solid. (UPLC-MS 1) tR 0.57 min; ESI-MS 154.0 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266883B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-94680d31a7d143e68caf4884a27b3b13
Source note	uspto-grants-2016_02