Lithium Chloride → HCID 68709474, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-bromo-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid ethyl ester F1 (0.497 mmol) in toluene (4 mL) and ethanol (4 mL), o -tolylboronic acid (0.75 mmol), LiCl (1.49 mmol), Na2CO3.10H2O (1.74 mmol) and (PPh3)2PdCl2 (3.5 mg) were added. The mixture was heated at 150° C. for 15 min with microwave irradiation then evaporated to dryness. Chromatography on silica gel (eluant: DCM/MeOH 95:5) afforded the title compound (85% yield). ESI (+) MS: m/z 333 (MH+). 1H NMR: 1.03 (d, J=7.07, 3H), 2.18 (s, 3H), 2.93 (t, J=7.40, 2H), 3.03 (t, J=7.30, 2H), 4.00 (q, J=7.07, 2H), 7.22-7.39 (m, 4H), 7.45 (d, J=5.12, 1H), 8.34 (d, J=5.00, 1H), 8.36 (s, 1H), 12.18 (bs, 1H). Employing the same methodology but using phenylboronic acid the following compound was prepared:

Provenance & Evidence