反应详情

To the product of step A (130 mg, 0.25 mmol) in dichloromethane, was added trifluoroacetic acid (0.48 mL) at 0° C. After stirring for 3 h, the reaction mixture was concentrated in vacuo, treated with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic extract was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography in (SiO2, 90:10 dichloromethane/methanol) and the free base treated directly with 1.25M HCl in methanol to give 6-chloro-8-(3-trifluoromethylphenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (28 mg, 27%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ 9.51 (s, 2H), 8.51 (d, J=1.5 Hz, 1H), 8.37-8.34 (m, 2H), 8.18 (d, J=1.5 Hz, 1H), 8.10 (d, J=7.8 Hz, 1H), 7.89 (t, J=7.8 Hz, 1H), 4.38 (s, 2H), 3.52 (t, J=5.2 Hz, 2H), 3.17 (t, J=5.4 Hz, 2H); APCI MS m/z 416 [M+H]+.

1. concentrationthe reaction mixture was concentrated in vacuo
2. additiontreated with saturated sodium bicarbonate solution
3. extractionextracted with dichloromethane
4. extractionThe organic extract
5. dry with materialwas dried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography in (SiO2, 90:10 dichloromethane/methanol)
8. additionthe free base treated directly with 1.25M HCl in methanol