Potassium Phosphate, Tribasic → HCID 11209970, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 3-ethyl-5-formyl-4-iodo-1H-pyrrole-2-carboxylate was obtained following the procedures described in Example 1. To a mixture of tert-butyl 3-ethyl-5-formyl-4-iodo-1H-pyrrole-2-carboxylate (0.0597 g, 0.172 mmol), K3PO4 (0.180 g, 0.85 mmol), Pd(PPh3)4(0.0120 g, 0.010 mmol), and 1-benzofuran-2-ylboronic acid (0.0330 g, 0.21 mmol) under N2 was added dimethoxyethane (2.5 mL). The reaction was heated to 85° C. and refluxed for 5 h. After cooling to ambient temperature, the reaction was filtrated through a pad of silica gel and concentration. The resultant residue was purified by normal phase chromatography (5-15% ethyl acetate/hexanes). Proton NMR for the product was consistent with the title compound as a 2:1 mixture of atropdiastereomers. 1H NMR (500 MHz, CDCl3) δ 10.17 (s, 0.7 H); 9.59 (s, 0.3H); 7.64 (app. d, J=7.6 Hz, 1H); 7.52 (app. d, J=8.1 Hz, 1H); 7.34 (app. t, J=7.7 Hz, 1H); 7.28 (app. t, J=7.6 Hz, 1H), 6.92 (s, 0.7H); 6.80 (s, 0.3H); 3.00 (q, J=7.3 Hz, 1.4H); 2.79 (q, J=7.5 Hz, 0.6H); 1.62 (s, 6.3H); 1.59 (s, 2.7H); 1.28 (t, J=7.3 Hz, 2.1H); 1.23 (t, J=7.6 Hz, 0.9H). HRMS (ES) exact mass calculated for C20H21NNaO4 (M+Na+): 362.1362. Found 362.1362.

Provenance & Evidence