Potassium Carbonate → 1-methyl-3-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d]imidazol-2(3H)-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one	HCID 590540	—
Reactant	2-(5-Chloropent-1-ynyl)pyridine	HCID 66598557	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-methyl-3-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d]imidazol-2(3H)-one	HCID 66598144	45.8%

Reaction Conditions

Temperature	-50 °C

Reaction Steps

2-(5-chloropent-1-ynyl)pyridine (59 mg, 0.33 mmol), 1-methyl-1H-benzo[d]imidazol-2(3H)-one (44 mg, 0.3 mmol) and K2CO3(70 mg, 0.511 mmol) were poured into DMF (0.45 mL) and the resulting mixture was heated at −50° C. overnight. The mixture was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM 100% as eluent) to afford 40 mg of 1-methyl-3-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d]imidazol-2(3H)-one as a yellow oil (Yield: 43%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08101637B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-3701df12cfed46039f0203ebd085ac9d
Source note	uspto-grants-2012_01