1-Methylpyrrolidine → methyl 4-ethyl-2-formyl-5-thien-2-yl-1H-pyrrole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate was obtained following the procedures described in Example 3. To a solution of methyl 4-ethyl-2-formyl-5-iodo-1H-pyrrole-3-carboxylate (0.123 g, 0.40 mmol) and bromo(thien-2-yl)zinc (0.1374 g, 0.60 mmol) in THF (2.0 mL) was added Pd(Pt-Bu3)2 (0.0123 g, 0.02 mmol) and N-methylpyrrolidine (2.0 mL). The reaction was deoxygenated by bubbling argon through the solution prior to being heated to 100° C. and refluxed for 4 h under argon. After cooling to ambient temperature, the reaction was filtered through a pad of silica gel and concentrated. The resultant residue was dissolved in acetonitrile and purified by reverse phase HPLC. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CDCl3) δ 10.14 (s, 1H); 7.42 (d, J=5.1 Hz, 1H); 7.24 (d, J=3.7 Hz, 1H); 7.14 (dd, J=3.7, 4.7 Hz, 1H); 3.94 (s, 3H); 2.94 (q, J=7.4 Hz, 2H); 1.24 (t, J=7.4 Hz, 3H). HRMS (ES) exact mass calculated C13H14NO3S (M+H): 264.0689. Found 264.0688

Provenance & Evidence