Hydrochloric Acid → HCID 66704132, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (105 mg, 0.448 mmol), (6-bromo-1H-indol-3-yl)-acetic acid methyl ester (100 mg, 0.373 mmol), tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.021 mmol), DMF (1.2 mL), ethanol (0.6 mL) and 2M aqueous potassium carbonate (0.6 mL) is heated to 80° C. for 6 hours. The reaction is cooled to room temperature, diluted with water, and acidified with 1 N HCl. The resulting solution is extracted with CH2Cl2. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated. The residue is purified via radial chromatography eluting with CH2Cl2. A second purification of impure fractions is performed via radial chromatography eluting with 2% MeOH—CH2Cl2 to provide (78 mg, 74%) of the title compound. LC-ES/MS m/e 296.0 (M+1).

Provenance & Evidence