Compound A12

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Compound data: NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

2-(o-tolyl)pyridine 1 and NMP were dried over 4 Å molecular sieves and degassed with 3 freeze-pump-thaw cycles prior to use. KOAc and K₂CO₃ were dried at 140 °C in a vacuum oven for 48 h prior to use. In a glove box, an oven-dried 250 mL round-bottom flask equipped with a magnetic stirring bar was charged with Ru9 (496.1 mg, 0.911 mmol, 3 mol %,), Clomipramine • HCl (10.671 g, 30.374 mmol, 1.0 equiv), 1 (5.294 g, 31.285 mmol, 1.03 equiv), KOAc (894.4 mg, 9.112 mmol, 0.3 equiv), K₂CO₃ (12.594 g, 91.122 mmol, 3 equiv) and NMP (30.4 mL, 1 M). The flask was sealed with a septa and the reaction was stirred at 35 °C for 48 h. Upon completion, the flask was transferred out of the glove box, the crude mixture was diluted with Et₂O (400 mL) and filtered with a short plug of Celite^®. The resulting organic mixture was washed with H₂O (200 mL, ×3 times) and the combined aqueous phases were extracted with Et₂O (200 mL, ×2 times). The combined organic phases were acidified with HCl (1M, 200 mL) and the aqueous layer was washed with EtOAc (150 mL, ×2 times), CH₂Cl₂ (150 mL, ×4 times), and Et₂O (150 mL, ×2 times). Then, the aqueous phase was basified with NaOH solution (1M, 300 mL), extracted with Et₂O (200 mL, ×4 times), washed with brine, dried over MgSO₄, and evaporated to dryness to afford A12 as an off-white solid (12.916 g, 95%).