Triethylamine → Methyl 6-amino-1,3-dihydro-2-benzofuran-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

Add palladium (II) acetate (2.8 mmol), 1,1-bis(diphenylphosphino)ferrocene (2.8 mmol), potassium carbonate (86.1 mmol), and triethyl amine (28.7 mmol) to a solution of 6-iodo-1,3-dihydro-isobenzofuran-5-ylamine (28.7 mmol) in acetonitrile (150 mL) and methanol (75 mL). Using a balloon of carbon monoxide, vacuum purge the reaction mixture several times, then heat to 70° C. After heating under a balloon of carbon monoxide for 1.5 h, cool the reaction to room temperature. Dilute the reaction with ethyl acetate (500 mL), wash with water (3×100 mL), followed by brine. Dry the organic phase over sodium sulfate, filter, and remove the solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-35%) to provide the title compound as an off white solid. 1H NMR (CDCl3, 400 MHz) δ 3.85 (s, 3H), 4.97 (s, 4H), 6.54 (s, 1H), 7.71 (s, 1H).

Provenance & Evidence