Sodium Hydroxide → HCID 89690439, compound

Temperature

-78 °C

To a solution of 2-cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine (742 mg) in THF (25 ml) was added n-butyllithium (1.6 M in hexane, 6.2 ml) at −78° C. The mixture was stirred at −78° C. under N2 atmosphere for 30 min. After being stirred, boric acid triisopropyl ester (0.86 ml) was added to the reaction mixture at −78° C. The mixture was stirred at −78° C. under N2 atmosphere for 30 min and then at room temperature for 3 h. The mixture was poured into 1 M NaOH at 0° C. and washed with EtOAc. The aqueous layer was neutralized with 1 M HCl (to pH 7.0) and extracted with EtOAc/IPA. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting solid was washed with EtOAc/MeOH to give the title compound (176 mg) as a yellow solid.

1. stirringAfter being stirred
2. stirringThe mixture was stirred at −78° C. under N2 atmosphere for 30 min
3. waitat room temperature for 3 h
4. washwashed with EtOAc
5. extractionextracted with EtOAc/IPA
6. customThe organic layer was separated
7. washwashed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo
10. washThe resulting solid was washed with EtOAc/MeOH

ORD record

ord-976cdd4e408f475e9e7cd981177fcce4

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2