Potassium Carbonate → Tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Chloro-1,3-benzothiazole-6-carboxamide	HCID 57553403	—
Reactant	tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate	HCID 86626541	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate	HCID 86626543	47.7%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 2-chloro-1,3-benzothiazole-6-carboxamide (77 mg, 0.36 mmol), tert-butyl[5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate (0.174 g, 0.54 mmol), Pd(dppf)Cl2*DCM (30 mg, 0.036 mmol) and 2 M aq. K2CO3 (0.8 mL) in DMF (2 mL) was stirred under argon at 80° C. for 2 h. The reaction mixture was filtered and the filtrate was partitioned between EtOAc and H2O. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (Heptane/EtOAc gradient) gave the product (66 mg) as a white solid. MS m/z (M−H) 383.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163928B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-94b465f84f4d4f65a2afb4115f57a524
Source note	uspto-grants-2012_04