Hydrochloric Acid → HCID 57585037, compound

Participants

Reaction Steps

A 5 mL conical microwave vessel was charged with 6-(6-chloro-5-((2-methoxyethoxy)methoxy)pyridin-3-yl)benzo[d]thiazole (0.0231 g, 0.0658 mmol), 2 mL TFE, 2M HCl (0.0329 ml, 0.0658 mmol), and a stirbar. The vessel was flushed with nitrogen, and then sealed. The reaction was irradiated using a Biotage microwave synthesizer to 100° C. for 15 minutes, and cooled. The solution was concentrated to half volume under a stream of nitrogen, and diluted with 1 mL 10% aqueous EtOH. The slurry was stirred at room temperature overnight, and cooled to −5° C. in a refrigerator. The precipitate was collected using a glass frit with a 0.22 μm PTFE syringe filter attached and positive pressure nitrogen. The solids were washed with 1 mL 10% aqueous EtOH, and then dried under a stream of nitrogen for 2 h. The solids were dissolved in DMF (2×2 mL), and filtered through the PTFE membrane. The solvent was removed in vacuo to afford 5-(benzo[d]thiazol-6-yl)-2-chloropyridin-3-ol (0.0159 g, 91.9% yield). 1H NMR (400 MHz, DMF) δ ppm 7.77 (d, J=2.13 Hz, 1H) 7.90 (dd, J=8.53, 1.76 Hz, 1H) 8.22 (d, J=8.41 Hz, 1H) 8.35 (d, J=2.13 Hz, 1H) 8.60 (d, J=1.00 Hz, 1H) 9.52 (s, 1H) 11.20 (s, 1H). 13C NMR (101 MHz, DMF) δ ppm 121.32 (s, 1 C) 122.52 (s, 1 C) 123.86 (s, 1 C) 125.82 (s, 1 C) 134.31 (s, 1 C) 135.34 (s, 1 C) 136.79 (s, 1 C) 138.14 (s, 1 C) 138.21 (s, 1 C) 150.44 (s, 1 C) 153.79 (s, 1 C) 157.01 (s, 1 C). HPLC-MS: 1.63 min (98.5%@215 nm; 97.9% @254 nm; m/z=262.9, calculated for C12H7ClN2OS+H+=263.0).

Provenance & Evidence