Pyridine → HCID 58914753, compound

Participants

Reaction Steps

Using a method similar to Preparation 38, with isatin (2.94 g, 20 mmol), 3-methoxyphenylboronic acid (6.08 g, 40 mmol), copper (II) acetate (3.63 g, 20 mmol), pyridine (3.2 ml, 40 mmol) and powdered 4A sieves (15-25 g) in dichloromethane (60 mL). Follow reaction by TLC (50% ethyl acetate/hexane). Stir mechanically for 1 day and add more powdered 4A sieves (10-15 g). Stir for 3 days and add 3-methoxyphenylboronic acid (1.52 g, 10 mmol), copper (II) acetate (1.82 g, 10 mmol), pyridine (1.6 ml, 20 mmol) and powdered 4A sieves (10-15 g). Workup and purify by flash chromotagraphy (dichloromethane) to provide 4.09 g (81%) of an orange solid. MS (ES): m/z=254 (M+1); 1H NMR (DMSO-d6): δ7.66-7.58 (m, 2H), 7.51 (t, 1H), 7.19 (t, 1H), 7.09-7.04 (m, 3H) 6.85 (d, 1H), 3.80 (s, 3H).

Provenance & Evidence