Pyridine → 1-(4-Isopropoxyphenyl)-5-(5-(trifluoromethyl)pyrid-2-yl)indole-2-carboxylic acid ethyl ester

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Reaction Steps

Anhydrous CH2Cl2 (10 mL), followed by Et3N (92 μL, 0.66 mmol), pyridine (54 μL, 0.66 mmol) and 3 Å molecular sieves (1 g) were added to a mixture of 5-(5-(trifluoromethyl)pyrid-2-yl)indole-2-carboxylic acid ethyl ester (110 mg, 1.33 mmol; see step (b)), Cu(OAc)2 (120 mg, 0.66 mmol), and 4-isopropoxyphenylboronic acid (119 mg, 0.66 mmol). The mixture was stirred vigorously at ambient temperature for 18 h after which additional Cu(OAc)2 (59.9 mg, 0.33 mmol), 4-isopropoxyphenylboronic acid (59.4 mg, 0.33 mmol), Et3N (46.4 μL, 0.33 mmol) and pyridine (27 μL, 0.33 mmol) were added. After a further 30 h of stirring, the mixture was filtered through Celite®. The filter cake was washed with EtOAc and the solvents concentrated and purified by chromatography to give the sub-title compound.

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