Sodium Chloride → 5-Fluoro-1-(2-fluorobenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridine

141 g (462.11 mmol) of the compound from Example 23A were initially charged in DMF (2538 ml), and 96.09 g (508.32 mmol) of 2-fluorobenzyl bromide and 165.62 g (508.32 mmol) of cesium carbonate were then added. The mixture was stirred at RT for two hours. The reaction mixture was then poured into saturated aqueous sodium chloride solution (13 670 ml) and extracted twice with ethyl acetate (5858 ml). The collected organic phases were washed with saturated aqueous sodium chloride solution (3905 ml), dried, filtered and concentrated. The residue was chromatographed on silica gel (eluent: 97:3 petroleum ether/ethyl acetate) and the product fractions were concentrated. The resulting solid was dissolved in dichloromethane and washed once with saturated aqueous sodium thiosulfate solution (500 ml) and then with saturated aqueous sodium chloride solution (500 ml). The product was concentrated to dryness and the residue was suspended in diethyl ether, isolated by filtration with suction and dried under high vacuum. This gave 106.6 g (62% of theory) of the title compound.

1. extractionextracted twice with ethyl acetate (5858 ml)
2. washThe collected organic phases were washed with saturated aqueous sodium chloride solution (3905 ml)
3. customdried
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was chromatographed on silica gel (eluent: 97:3 petroleum ether/ethyl acetate)
7. concentrationthe product fractions were concentrated
8. dissolutionThe resulting solid was dissolved in dichloromethane
9. washwashed once with saturated aqueous sodium thiosulfate solution (500 ml)
10. concentrationThe product was concentrated to dryness
11. customisolated by filtration with suction
12. customdried under high vacuum

ORD record

ord-6ad8df4c1d2f48eb9e3bd3cfb4bcbdaa

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096592B2