Hydrochloric Acid → Tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate

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To a solution of tert-butyl 2-chloro-5-(diphenylmethyleneamino)pyridin-3-ylcarbamate (0.280 g, 0.686 mmol) in THF (5 mL) was added hydrochloric acid, In (JT Baker) (0.031 mL, 1.030 mmol). The reaction was stirred at rt in closed system for 20 min. The reaction mixture was partitioned between EtOAc/sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (24 g, 3% MeOH in DCM) to afford the desired product as a white foam-like solid (135.0 mg). MS (ESI pos. ion) m/z: 244.1. 1H NMR (300 MHz, CDCl3) δ ppm 1.54 (s, 9H) 3.73 (br. s., 2H) 6.93 (br. s., 1H) 7.52 (d, J=2.63 Hz, 1H) 7.94 (d, J=2.63 Hz, 1H).

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