反应详情

To a solution 6-bromo-2-(bromomethyl)thiazolo[5,4-b]pyridine (800 mg, 2.60 mmol) (Journal of Medicinal Chemistry, 53(10), 3927-3936; 2010) in tetrahydrofuran (10 mL) is added ammonium hydroxide (2 mL) and stirred at room temperature for 16 hours. Reaction is concentrated, diluted with water (5 mL) and extracted using ethyl acetate (3×10 ml). Extracts are dried over Na2SO4 and concentrated to get crude product (650 mg). m/z (CI) M+244. To a solution of crude amine (350 mg, 1.43 mmol) in tetrahydrofuran (10 mL) and aqueous NaHCO3 (2 mL) is added boc anhydride and resulting mixture stirred at room temperature for over night. Organic solution is separated and aqueous layer extracted with ethyl acetate (5 mL). Combined organic solution is dried over Na2SO4 and concentrated under vacuum to give the title compound (400 mg): 1H NMR (400 MHz, CDCl3) 1.50 (s, 9H), 4.74 (d, 2H), 8.36 (s, 1H), 8.62 (s, 1H). m/z (CI) M+2 346.

1. customReaction
2. concentrationis concentrated
3. additiondiluted with water (5 mL)
4. extractionextracted
5. dry with materialExtracts are dried over Na2SO4
6. concentrationconcentrated
7. customto get crude product (650 mg)
8. customresulting mixture
9. stirringstirred at room temperature for over night
10. customOrganic solution is separated
11. extractionaqueous layer extracted with ethyl acetate (5 mL)
12. dry with materialCombined organic solution is dried over Na2SO4
13. concentrationconcentrated under vacuum