Thionyl Chloride → (5-Tert-butyl-2-methoxy-phenyl)-[5-(2,6-diethyl-phenyl)-pyrrolo-[2,3-c]pyridine-1-yl]-methanone

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Reaction Conditions

Reaction Steps

Thionyl chloride (0.3 mL, excess) is added dropwise to a solution of 5-tert-butyl-2-methoxy-benzoic acid (30 mg, 0.2 mmol) in CH2Cl2 (1 mL) at room temperature. The mixture is heated to 60° C. for 1.5 hours. The solvent is removed to dryness. A solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (10 mg, 0.04 mmol) and N,N-diisopropylethylamine (0.2 mL, excess) in THF (1 mL) is added to the residue. The mixture is stirred at room temperature for 16 hours. The solvent is removed to dryness in vacuo. The crude product is purified by PTLC and eluted with 20% EtOAc in hexane to give 12 mg of (5-tert-butyl-2-methoxy-phenyl)-[5-(2,6-diethyl-phenyl)-pyrrolo-[2,3-c]pyridine-1-yl]-methanone. 1H NMR (CDCl3) 7.56-6.98 (m, 9H), 6.60-6.58 (d, 1H), 3.81 (s, 3H), 2.41-2.24 (q, 4H), 1.31 (s, 9H), 1.08-1.00 (t, 3H).

Provenance & Evidence