Potassium Carbonate → N-tert-butoxycarbonyl-amino-2-(5-nitro-2-pyridinylthio)ethane

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Reaction Steps

A heterogeneous solution of 2-mercapto-5-nitropyridine (96 mg, 0.62 mmol), N-tert-butoxycarbonyl-amino-2-bromoethane (0.14 g, 0.63 mmol), and K2CO3 (0.42 g, 3.0 mmol) in acetone (10 mL) was heated at 60° C. for 15 h. The cooled reaction mixture was filtered through Celite®, concentrated, and then purified by silica gel chromatography to give N-tert-butoxycarbonyl-amino-2-(5-nitro-2-pyridinylthio)ethane (37), which was treated with trifluoroacetic acid (5 mL) in dichloromethane (5 mL) at room temperature for 30 min. The reaction mixture was concentrated and then residue was suspended in dichloromethane, washed with saturated NaHCO3 followed by brine, dried over anhydrous MgSO4 and concentrated to give 1-amino-2-[(5-nitro-2-pyridinyl)thio]ethane (38) as a tan solid which was used without further purification. 1H NMR (DMSO-d6): δ 9.21 (d, J=3.0 Hz, 1H), 8.41 (dd, J=2.4 and 8.7 Hz, 1H), 7.81 (bs, 2H), 7.65 (d, J=8.7 Hz, 1H), 3.44 (t, J=6.6 Hz, 2H), 3.12 (t, J=6.6 Hz, 2H).

Provenance & Evidence