2,6-Dichloro-4-iodopyridine → Methyl 2-(4-((2,6-dichloropyridin-4-yl)ethynyl)phenyl)cyclopropanecarboxylate

Participants

Reaction Steps

The title compound was prepared from methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate (80 mg, 0.40 mmol) and 2,6-dichloro-4-iodopyridine (121 mg, 0.44 mmol) according to the general procedure IF to give 19 mg (23%) of a white solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:10): Rf=0.36 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.45 (d, J=8.2 Hz, 2H), 7.34 (s, 2H), 7.11 (d, J=8.2 Hz, 2H), 3.73 (s, 3H), 2.61-2.48 (m, 1H), 2.02-1.90 (m, 1H), 1.67 (dt, J=10.0, 5.1 Hz, 1H), 1.35 (ddd, J=8.4, 6.4, 4.8 Hz, 1H); 13C NMR (CDCl3) δ 173.4, 150.7, 142.5, 136.5, 132.2, 126.4, 124.4, 119.2, 96.7, 84.7, 52.1, 26.1, 24.4, 17.3; ESI-MS m/z 368.1 (M+Na+).

Provenance & Evidence