Water → 1H-pyrrolo[3,2-c]pyridine-4-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	N-methyl-2-pyrrolidone	HCID 13387	—
Reactant	4-chloro-1H-pyrrolo[3,2-c]pyridine	HCID 14114384	—
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	—
Product	1H-pyrrolo[3,2-c]pyridine-4-carbonitrile	HCID 26076432	32%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 4-chloro-1H-pyrrolo[3,2-c]pyridine (500 mg, 3.28 mmol), zinc cyanide (422 mg, 3.61 mmol), Pd2(dba)3 (600 mg, 0.656 mmol), dppf (729 mg, 1.312 mmol), and Zn powder (21 mg, 0.328 mmol) in NMP (30 mL) under nitrogen was stirred at 120° C. for 18 h. The reaction mixture was cooled, poured into water (150 mL), extracted with DCM (3×50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (1:1) as eluting solvents to afford 1H-pyrrolo[3,2-c]pyridine-4-carbonitrile as a white solid (150 mg, 32%). MS (ESI) m/z: 144.3 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815877B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-17452629810a4ce88190cdd652730f6d
Source note	uspto-grants-2014_08