Dimethylformamide → Thiazolo[5,4-b]pyridine-5-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	HCID 23371316	HCID 23371316	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Product	Thiazolo[5,4-b]pyridine-5-carbonitrile	HCID 67305386	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To an 8 mL screw cap vial equipped with a magnetic stirring bar were added 5-chlorothiazolo[5,4-b]pyridine (Q-4) (460 mg, 2.7 mmol), Zn(CN)2 (316 mg, 2.7 mmol), Pd2(dba)3 (123 mg, 0.13 mmol), DPPF (150 mg, 0.27 mmol) and DMF (5 mL, wet, containing 1% of H2O). The vial was flushed with nitrogen, then sealed with the screw cap. The mixture was stirred at 120° C. for overnight, and then concentrated in vacuo. The resulting residue was purified by chromatography on silica gel to give the title compound (151 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08507487B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-457d2997448a4bbd824868adf76d00e1
Source note	uspto-grants-2013_08