Dichloromethane → 6-Bromo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

1.075 g 4-Iodo-3-methoxy-6-pyridin-4-yl-pyridazine, 1.45 g 6-bromo-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester, 4.48 g cesium carbonate, and 140 mg [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) complex with dichloromethane (1:1) are dissolved in a mixture of 30 mL dioxane and 8.8 mL water. Argon is bubbled through the solution for 5 minutes. The mixture is heated to reflux for 2 hours. After diluting with EtOAc, the organic phase is washed with water and brine, dried with MgSO4 and concentrated in vacuo. Purification on silica (Flashmaster, methylenechloride/MeOH) gives 1.59 g (96%) 6-bromo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester.

Provenance & Evidence