Water → HCID 58803197, compound

Temperature

25 °C

To a solution of methyl 1H-indole-5-carboxylate (1.5 g) in DMF (30 mL) was added NaH (410 mg) at 0° C. The reaction mixture was warmed to 25° C., followed by stirring for 0.5 hours. Then, the reaction mixture was cooled to 0° C. again, and then methyliodide (1.38 mL) was added thereto. The reaction mixture was warmed to 25° C., followed by stirring for 3 hours. To the reaction liquid was added water (50 mL), followed by extraction with EtOAc (50 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, CHCl3:MeOH=100:0 to 98:2) to obtain methyl 1-ethyl-1H-indole-5-carboxylate (1465 mg) as a white solid.

1. temperatureThen, the reaction mixture was cooled to 0° C. again
2. temperatureThe reaction mixture was warmed to 25° C.
3. stirringby stirring for 3 hours
4. customTo the reaction liquid
5. extractionfollowed by extraction with EtOAc (50 mL) three times
6. washThe organic layer was washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (automatic purification device, CHCl3:MeOH=100:0 to 98:2)

ORD record

ord-ee353fad36ee447e92b1356a56e9979b

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193378B2