Boron tribromide → HCID 59436022, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2,6-dichloro-4-iodophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (200 mg, 0.40 mmol) were added 1H-pyrazol-5-ylboronic acid (48 mg, 0.43 mmol) 2.0 M solution of NaHCO3 (1 mL) and tetrakis(triphenylphosphine)palladium (0) (90 mg, 0.78 mmol) and the mixture was heated to 80° C. for 4 hr. After cooling to room temperature, the reaction mixture was extracted with EtOAc and water. Column chromatography (100% Hex to 100% EtOAc) afforded the cross-coupled product. This purified material (79 mg) was taken up in chloroform (5 mL) followed by the addition of BBr3 (1.40 mL, 1M in CH2Cl2) and heated to 85° C. for 1 hr. The solution was cooled to room temperature, extracted with 3:1 CHCl3/IPrOH and washed with saturated NaHCO3. The organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography (100% CH2Cl2 to 35% MeOH/65% CH2Cl2) afforded the title compound as a mixture of rotamers.

Provenance & Evidence