Potassium Cyanide → 1H-pyrazolo[3,4-b]pyridine-4-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Potassium Cyanide	HCID 9032	—
Reactant	p-Toluenesulfinic acid	HCID 10818	—
Reactant	Sodium	HCID 5360545	—
Reactant	4-Iodo-1H-pyrazolo[3,4-b]pyridine	HCID 57642801	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Product	1H-pyrazolo[3,4-b]pyridine-4-carbonitrile	HCID 69434551	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-Iodo-1H-pyrazolo[3,4-b]pyridine (802 mg, 3.27 mmol) was dissolved in DMSO (10 mL) then added p-toluenesulfinic acid, sodium salt (583 mg, 3.27 mmol) and KCN (319 mg, 4.90 mmol). The reaction was heated at 100° C. for 18 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4 to yield 1H-pyrazolo[3,4-b]pyridine-4-carbonitrile as a light orange solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08247556B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-10ad59d1faea44eea63578b42f319edf
Source note	uspto-grants-2012_08