Cesium carbonate → Tert-butyl 2-[(4-{[4-(dimethylamino)phenyl]ethynyl}phenyl)acetyl]hydrazinecarboxylate

To a mixture of 4-bromo-N,N-dimethylaniline (175 mg, 0.88 mmol), cesium carbonate (476 mg, 1.46 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (22 mg, 0.04 mmol) and bis(acetonitrile)dichloropalladium (II) (10 mg, 0.04 mmol) was added anhydrous acetonitrile (2 ml), and the mixture was stirred at room temperature for 15 mins. A solution of tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate (200 mg, 0.73 mmol) in anhydrous acetonitrile (4 ml) was added, and the mixture was stirred at 80° C. for 5 hrs. After cooling, the reaction mixture was filtered, and the insoluble material was washed with ethyl acetate. The filtrate and washing solution were combined and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (chloroform:methanol=97:3) to give tert-butyl 2-[(4-{[4-(dimethylamino)phenyl]ethynyl}phenyl)acetyl]hydrazinecarboxylate (110 mg, yield 38%) as a yellow solid.

1. stirringthe mixture was stirred at 80° C. for 5 hrs
2. temperatureAfter cooling
3. filtrationthe reaction mixture was filtered
4. washthe insoluble material was washed with ethyl acetate
5. washThe filtrate and washing solution
6. concentrationconcentrated under reduced pressure
7. customThe concentrated residue was purified by silica gel column chromatography (chloroform:methanol=97:3)

ORD record

ord-4f5454c0934b4e60b06dbdc03116b095

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999989B2