Pyridine → HCID 86683606, compound

Participants

Reaction Steps

In a 15 mL reaction tube was added tert-butyl (1-(4-(2,2-dioxido-7-phenyl-1H-pyrido[3,2-e][1,3,4]oxathiazin-6-yl)phenyl)cyclobutyl)carbamate (50 mg, 0.099 mmol), pyridin-3-ylboronic acid (24 mg, 0.197 mmol), copper(II)acetate (27 mg, 0.148 mmol) and 5 Å molecular sieves (30 mg) in anhydrous dichloromethane (1 ml). To this was added anhydrous pyridine (16 μl, 0.197 mmol) and the resulting black suspension stirred at room temperature under air for 24 hours. Further pyridine (1 mL) was added and the resulting black solution stirred at room temperature for 24 hours. Further pyridin-3-ylboronic acid (24 mg, 0.197 mmol) and copper (II)acetate (27 mg, 0.148 mmol) were added and the mixture stirred at room temperature for 72 hours. The reaction mixture was concentrated to dryness under reduced pressure and the residue purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 88:12 to 0:100) to give the desired product as an off-white solid (40 mg 70% yield). 1H-NMR (500 MHz, CDCl3) δ 8.67-8.76 (2H, m), 7.89 (1H, d), 7.54 (1H, dd), 7.20-7.35 (7H, m), 7.06 (2H, d), 7.03 (1H, s), 5.38 (2H, s), 5.07 (1H, br s), 2.20-2.60 (4H, m), 2.00-2.15 (1H, m), 1.78-1.90 (1H, m), 1.10-1.50 (9H, br s). LCMS (Method A) RT=6.98 min, M+H+=584.99.

Provenance & Evidence