Dimethylformamide → (3-Cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	(3-Iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester	HCID 57978086	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Product	(3-Cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester	HCID 57978082	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

A 250 mL flask was charged with (3-iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester (15.0 g), PdCl2(dppf) (3.0 g), Zn(CN)2 (4.96 g), DMF (200 mL) and H2O (14 mL). The flask containing the resultant suspension was degassed and backfilled with nitrogen gas repeatedly for 5 minutes, followed by addition of Pd2(dba)3 (3.85 g) to the reaction mixture. The reaction mixture was heated under N2 at 90° C. for 16 h, cooled to room temperature, diluted with H2O (800 mL) and filtered. The collected solid was washed with toluene (10 mL) to provide (3-cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08481545B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-063e2f79239540b2bb3eb2fd1f58e869
Source note	uspto-grants-2013_07