HCID 117720296, compound → HCID 117720122, compound

Temperature

-78 °C

To a stirred solution of the product of Example 13b (95 mg, 0.33 mmol) in anhydrous tetrahydrofuran (6 mL) under argon at −78° C. was added methyl lithium (1.6 M in diethyl ether) (1.04 mL, 1.66 mmol). The reaction was stirred at −78° C. for 1 hour, after which the reaction was allowed to warm gradually to room temperature and stirring was continued overnight. The reaction was quenched with saturated aqueous ammonium chloride (25 mL) and the organics were extracted with ethyl acetate (25 mL×3). The combined organic phase was washed with brine (40 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->5/1) afforded 30 mg of the impure title compound as a yellow oil which was used directly in the next step. Mass spectrum (ESI +ve) m/z 302 (M+H+).

1. temperatureto warm gradually to room temperature
2. stirringstirring
3. waitwas continued overnight
4. customThe reaction was quenched with saturated aqueous ammonium chloride (25 mL)
5. extractionthe organics were extracted with ethyl acetate (25 mL×3)
6. washThe combined organic phase was washed with brine (40 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customPurification of the residue by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->5/1)

ORD record

ord-ebbf87a982114e19bd9bb8233bccdeed

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353063B2