反应详情

温度

0 °C

To a mixture of NaH (38 mg, 1.6 mmoles) in THF (5 ml) at ambient temperature was added 4-chloro-3-methyl-5-amino isoxazole (84 mg, 0.63 mmoles). The mixture was stirred 1 hr. at ambient temperature then cooled to 0° C. followed by the addition of 2-ethylthieno[2,3-b]pyridine-3-sulfonyl chloride (0.19 g, 0.73 mmoles) via cannula in THF (2 ml). The cooling bath was removed and the brown mixture was stirred 1 hr. at ambient temperature and then diluted with 3% NaOH (50 ml) and washed with CHCl3 (2×75 ml). The aqueous layer was acidified to pH 4 using concentrated HCl, upon which a precipitate formed. The aqueous phase was extracted with EtOAc (50 ml), and the organic layer was dried (MgSO4), filtered and concentrated to collect 0.23 g of a yellow oil. Recrystallization from EtOAc/hexanes provided 0.18g (79%) of the title compound as a light yellow solid, m.p. 152°-154° C.

1. customThe cooling bath was removed
2. stirringthe brown mixture was stirred 1 hr
3. additionat ambient temperature and then diluted with 3% NaOH (50 ml)
4. washwashed with CHCl3 (2×75 ml)
5. customupon which a precipitate formed
6. extractionThe aqueous phase was extracted with EtOAc (50 ml)
7. dry with materialthe organic layer was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customto collect 0.23 g of a yellow oil
11. customRecrystallization from EtOAc/hexanes