Potassium Carbonate → 6-Chloro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole

https://huagongshe.com/reaction/1960148

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1-Methyl-1H-indole-5-boronic acid	HCID 2759867	—
Reactant	5-chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole	HCID 57481466	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	6-Chloro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole	HCID 67447355	—

Reaction Steps

To a microwave reactor vial was added 6-chloro-5-iodo-2-(methylsulfonyl)-1H-benzimidazole 16-5 (2 g, 5.6 mmol), PdCl2(dppf) (205 mg, 8.4 mmol), K2CO3 (2.32 g 17 mmol), 1-methyl-5-indoleboronic acid (1.47 g, 8.4 mmol) in 20 mL of toluene and 6 mL H2O. The reaction was run in a microwave reactor for 7 min at 130° C. The reaction mixture was diluted with EtOAc (150 mL) and washed three times with 150 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Then CH2Cl2 was added and the desired product precipitated out of the solution. The resulting solid was collected by vacuum filtration and washed with copious amounts of CH2Cl2 to yield the title compound 16-6 as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08410284B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-dceb649e0d9f448898576e092ecf3664
Source note	uspto-grants-2013_04