Dichloromethane → HCID 86664053, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Ethyl 1-(4-bromothiazol-2-yl)-4-ethyl-piperidine-4-carboxylate	HCID 66977057	—
Reactant	2-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-ylboronic acid	HCID 72724483	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86664053	HCID 86664053	36%

Reaction Conditions

Temperature	120 °C

Reaction Steps

Ethyl 1-(4-bromothiazol-2-yl)-4-ethyl-piperidine-4-carboxylate (56 mg, 0.16 mmol), 2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl-boronic acid (50 mg, 0.15 mmol), and cesium carbonate (42 mg, 0.22 mmol) were suspended in DMF (1 mL) in a 5 mL microwave vessel. The resulting mixture was degassed with Ar for 5 min. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (10 mg, 0.01 mmol), was added to the mixture, then the vessel sealed and heated at 120° C. for 60 min in a microwave. The mixture was cooled to rt then evaporated to dryness and the crude residue purified over a 12 g silica-gel column using a MeOH: DCM elution gradient (0-5%) to obtain the product as a viscous oil (30 mg, 36% yield). MS: 565.13 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181234B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-155c946d6c2b4b579265ee66295d9062
Source note	uspto-grants-2015_11