Methyl iodide → HCID 67378219、化合物

6,7-Dichloro-9-tosyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 0.1 g, 0.024 mmol) was dissolved in dry THF, cooled to −78° C. and LiHMDS (0.6 mL, 0.61 mmol) was added dropwise. The reaction mixture was slowly warmed to 0° C. and stirred for an additional 30 min. The reaction mixture was cooled to −78° C. and MeI (0.040 mL, 0.61 mmol) was added slowly, warmed to room temperature and stirred for 4 h. Saturated NH4Cl (10 mL) was added to the reaction mixture and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography [EtOAc-hexane (1:9) as eluant] to obtain the title compound (0.04 g, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.49 (s, 1H), 8.03 (d, J=8.0 Hz, 2H), 7.67 (s, 1H), 7.32 (d, J=8.0 Hz, 2H), 2.98-2.85 (m, 2H), 2.71-2.66 (m, 1H), 2.43 (s, 3H), 2.27-2.23 (m, 1H), 1.96-1.89 (m, 1H), 1.25-1.17 (m, 3H).

1. temperatureThe reaction mixture was slowly warmed to 0° C.
2. temperatureThe reaction mixture was cooled to −78° C.
3. temperaturewarmed to room temperature
4. stirringstirred for 4 h
5. extractionextracted with EtOAc (2×50 mL)
6. dry with materialThe combined organic extracts were dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe crude residue was purified by column chromatography [EtOAc-hexane (1:9) as eluant]

ORDレコード

ord-fd3bd2faff3c47caaf48b72b586208f4

出典データセット

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08987319B2