Sodium Carbonate → HCID 66990281, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-Bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester (143 mg, 0.53 mmol), bis(pinacolato)diboron (202 mg, 0.79 mmol), tricyclohexylphosphine (15 mg, 0.053 mmol), potassium acetate (105 mg, 1.07 mmol) and Pd(dba)2 (15 mg, 0.027 mmol) in 1,4-dioxane (5 ml) is heated to 110° C. in an oil bath for 1 hour under argon. 4-Bromo-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid(pyridin-4-ylmethyl)-amide (225 mg, 0.53 mmol) and (Bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (38 mg, 0.053 mmol) and aqueous Na2CO3 (2M, 1.33 ml, 2.65 mmol) are added, and the reaction mixture is heated at 110° C. for 1 hour. The mixture is cooled to room temperature, diluted with 5% methanol/dichloromethane and filtered through celite. The filtrate is evaporated in vacuo, and the crude product is purified by reverse phase HPLC to give the title compound 5-[5-Methyl-2-[(pyridin-4-ylmethyl)-carbamoyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester as a light yellow solid 150 mg, 53%, LC/MS ESI m/z (M+H)+=535.61.

Provenance & Evidence