Sodium Iodide → HCID 178505979, compound

Temperature

0 °C

10 g (65.75 mmol) of 5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-amine were initially charged in THF (329 ml), and the mixture was cooled to 0° C. 16.65 ml (131.46 mmol) of boron trifluoride diethyl ether complex were then added slowly. The reaction mixture was cooled further to −10° C. A solution of 10.01 g (85.45 mmol) of isopentyl nitrite in THF (24.39 ml) was then added slowly, and the mixture was stirred for a further 30 min. The mixture was diluted with cold diethyl ether (329 ml) and the resulting solid was isolated by filtration. A little at a time, the diazonium salt thus prepared was added to a cold (0° C.) solution of 12.81 g (85.45 mmol) of sodium iodide in acetone (329 ml), and the mixture was stirred at RT for 30 min. The reaction mixture was poured into ice-water (1.8 l) and extracted twice with ethyl acetate (487 ml each time). The collected organic phases were washed with saturated aqueous sodium chloride solution (244 ml), dried, filtered and concentrated. This gave 12.1 g (86% purity, 60% of theory) of the desired compound in the form of a brown solid. The crude product was reacted without further purification.

1. addition16.65 ml (131.46 mmol) of boron trifluoride diethyl ether complex were then added slowly
2. temperatureThe reaction mixture was cooled further to −10° C
3. customthe resulting solid was isolated by filtration
4. stirringthe mixture was stirred at RT for 30 min
5. extractionextracted twice with ethyl acetate (487 ml each time)
6. washThe collected organic phases were washed with saturated aqueous sodium chloride solution (244 ml)
7. customdried
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was reacted without further purification

ORD record

ord-b59f137a7f7a4abe9de334b87ffc10b3

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921377B2