2-Chloro-3-isothiocyanatopyridine → N-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

3-(Benzyloxy)-5-bromopyridin-2-amine (10.0 g, 35.83 mmol) was added to a mixture of 2-chloro-3-isothiocyanatopyridine (6.112 g, 35.83 mmol) in DMF. The reaction was stirred at 80° C. for an hour, then at 110° C. for two hours. The reaction was cooled, diluted in water (200 mL) and 2N NaOH (35 mL), stirred for 30 minutes, and then filtered. The wet solids were washed with water, then dissolved in dichloromethane (300 mL) dried over MgSO4, and filtered. Hexane (300 mL) was added to the combined filtrates, the mixture was concentrated to 500 mL, and then mixture stirred for 30 minutes. The mixture was filtered to afford the first crop of the title compound. The mother liquor was concentrated to 500 mL (until most of the dichloromethane was removed), filtered, washed with hexanes to afford a second crop of the title compound. The two crops combined afforded the title compound (10.2 g, 68.7%) as light yellow crystals: 1H NMR (CDCl3) δ 5.14 (s, 2H), 7.30-7.33 (m, 2H), 7.42-7.48 (m, 5H), 7.87 (d, 1H), 8.10 (s, 1H), 8.40 (d, 1H), 8.67 (bs, 1H).

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