Potassium Carbonate → HCID 57686382, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Bromo-1,3-benzothiazole	HCID 612040	—
Reactant	Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate	HCID 4642098	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	HCID 57686382	HCID 57686382	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of 2-bromo-benzothiazole (0.38 g, 1.1 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.5 g, 1.62 mmol), potassium carbonate (0.67 g, 4.85 mmol), Pd(dppf)Cl2 (0.132 g, 0.16 mmol) and 4/1/dioxane/water (10 ml) was degassed for 15 minutes. Then it was heated at 90° C. for overnight. Cooled to room temperature and diluted with EtOAc (200 mL). The organic layer was washed with water (100 ml), dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel to give the desired product 21BB (0.4 g, 78%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546404B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-079ca7fed79c4c67b3260579738cdc85
Source note	uspto-grants-2013_10