Sodium Carbonate → HCID 86606708, compound

Participants

Reaction Conditions

Reaction Steps

200 mg (0.50 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1-benzothiophene-2-carboxamide hydrochloride (Example 11A) and 74.6 mg (0.50 mmol) of 4-formylphenylboronic acid are introduced into 2 ml of DMF. Addition of 0.75 ml of 2 M sodium carbonate solution and 20.3 mg (0.02 mmol) of PdCl2(dppf) is followed by heating to 80° C. After 18 h, the reaction mixture is filtered through kieselguhr and purified by preparative HPLC. The product fractions are concentrated, mixed with a 5:1 mixture of methanol and 4 N hydrogen chloride in dioxane and again concentrated. Drying under high vacuum results in 163.8 mg (75.0% of theory) of the title compound.

Provenance & Evidence