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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	4-Bromo-1H-pyrrolo(2,3-c)pyridine	HCID 12510055	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Zinc	HCID 23994	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	1H-Pyrrolo[2,3-c]pyridine-4-carbonitrile	HCID 46835724	99.8%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 4-bromo-1H-pyrrolo[2,3-c]pyridine (320 mg, 1.62 mmol), Pd(dppf)Cl2 (131 mg, 0.179 mmol), zinc cyanide (190 mg, 1.62 mmol), and zinc powder (21 mg, 0.324 mmol) in DMF (20 mL) was stirred at 120° C. for 2 h. The reaction mixtue was cooled to RT and H2O (100 mL) was added. The reaction mixture extracted with EtOAc (3×50 mL). The organic layers were concentrated tinder reduced pressure and the crude residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (1:1) to afford 232 mg (99.8%) of 1H-pyrrolo[2,3-c]pyridine-4-carbonitrile as yellow solid: MS (ESI) m/z: 144.2 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815877B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-90888dc18bd7438aabe9f3f11607cc89
Source note	uspto-grants-2014_08