Triisopropyl borate → HCID 90100563, compound

Temperature

-78 °C

100 mg (1.0 eq) of the obtained 2-(3-fluorophenyl)-5-(methoxymethoxy)pyridine was dissolved in 4.3 mL of tetrahydrofuran. After cooling to −78° C., tert-butyllithium 1.7 M solution (0.5 mL, 2.0 eq) was added slowly. The mixture was stirred at the same temperature for 30 minutes. 121 mg (1.5 eq) of B(O-iPr)3 was dissolved in 2.1 mL of tetrahydrofuran, and added to the above mixture. The mixture was stirred at the same temperature for 1 hour, and stirred for 3 hours as warming to room temperature. After quenching by adding distilled water, tetrahydrofuran solution was added, and washed with brine. The reaction solution was dried with magnesium sulfate to remove water, concentrated under reduced pressure, and crystallized with methylchloride to obtain 50 mg of (2-(3-fluorophenyl)-5-hydroxypyridin-4-yl)boronic acid as white solid.

1. additionadded to the above mixture
2. stirringThe mixture was stirred at the same temperature for 1 hour
3. stirringstirred for 3 hours
4. temperatureas warming to room temperature
5. customAfter quenching
6. additionby adding
7. distillationdistilled water, tetrahydrofuran solution
8. additionwas added
9. washwashed with brine
10. dry with materialThe reaction solution was dried with magnesium sulfate
11. customto remove water
12. concentrationconcentrated under reduced pressure
13. customcrystallized with methylchloride

ORD record

ord-a0f5ad9de16b44f38c2beed1f2a1f337

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376429B2