Sodium Carbonate → HCID 67313210, compound

Participants

Reaction Conditions

Reaction Steps

3.89 ml of 2 M aqueous sodium carbonate solution and 105.9 mg (0.13 mmol) of PdCl2(dppf) are added to a mixture of 1000 mg (2.59 mmol) of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride (free base: Example 31A) and 430.2 mg (2.59 mmol) of 3-carboxyphenylboronic acid in 8 ml of DMF. The reaction mixture is heated at 70° C. for 18 h and then filtered through kieselguhr and evaporated to dryness. Purification of the crude product by preparative HPLC, subsequent addition of a 3:1 mixture of methanol and 1N hydrochloric acid, concentration and drying under high vacuum result in 142.5 mg (12% of theory) and a further 627.9 mg (of 80% purity) of the title compound.

Provenance & Evidence