Pentane → HCID 57517878, compound

Temperature

-78 °C

A 1.7 M solution of tert-butyllithium in pentane (35 ml, 60 mmol) was added to THF (100 ml) at −78° C. 2-Bromomesitylene (4.6 ml, 30 mmol) was added dropwise and the mixture stirred at −78° C. for 1 h. 2-Methoxypyridine (3.2 ml, 30 mmol) was added at −78° C. and then the mixture was stirred at 0° C. for 1.5 h. The ice-cold solution of the lithiated 2-methoxypyridine was transferred (via a transfer needle) into an ice-cold suspension of 5-iodoisatin (4.1 g, 15 mmol) in THF (150 ml). The reaction mixture was allowed to warm to room temperature and then saturated ammonium chloride solution was added. The mixture was extracted three times with ethyl acetate, and the collected extracts were washed with saturated brine. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by crystallization from dichloromethane yielded 2.9 g of the intermediate.

1. stirringthe mixture was stirred at 0° C. for 1.5 h
2. temperatureto warm to room temperature
3. extractionThe mixture was extracted three times with ethyl acetate
4. washthe collected extracts were washed with saturated brine
5. dry with materialThe organic phase was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customPurification
9. customby crystallization from dichloromethane

ORD record

ord-ca23f3e1ba8d4bb186a554c0da24884e

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580842B2