Dimethylformamide → HCID 67003649, compound

Temperature

0 °C

To an ambient solution of 5-methoxy-1H-indole (5 g, 34.0 mmol) in N,N-dimethylformamide (100 mL) was added a solution of bromine (1.75 mL, 34.0 mmol) in N,N-dimethylformamide (25 mL). The mixture was stirred for about 15 minutes. The mixture was cooled to about 0° C., and NaH (3.26 g, 82 mmol) was added in portions over 15 minutes. The mixture was stirred for 15 minutes, and then iodomethane (2.55 mL, 40.8 mmol) was added. The bath was removed and the slurry was warmed to room temperature. After about 45 minutes, the solvents were removed under reduced pressure, and the mixture was partitioned between dichloromethane (50 mL) and water (100 mL). The layers were separated, and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with dichloromethane, to give the title compound.

1. stirringThe mixture was stirred for 15 minutes
2. customThe bath was removed
3. temperaturethe slurry was warmed to room temperature
4. waitAfter about 45 minutes
5. customthe solvents were removed under reduced pressure
6. customthe mixture was partitioned between dichloromethane (50 mL) and water (100 mL)
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
9. dry with materialThe combined organics were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by chromatography on silica gel
13. washeluting with dichloromethane

ORD record

ord-e6b6336ba3b54be2bfa69bc0679af831

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691810B2