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 a nitrogen atmosphere for 30 min. Boric acid triisopropyl ester (0.86 mL) was added to the obtained mixture at −78° C. The mixture was stirred at −78° C. for 30 min and then at room temperature for 3 hr. The mixture was poured into 1 N sodium hydroxide at 0° C. and washed with ethyl acetate. The obtained aqueous layer was neutralized with 1 N hydrochloric acid to pH 7.0 and extracted with ethyl acetate/2-propanol. The obtained organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resulting solid was washed with ethyl acetate/methanol to give the title compound (176 mg) as a yellow solid.

1. stirringThe mixture was stirred at −78° C. for 30 min
2. waitat room temperature for 3 hr
3. washwashed with ethyl acetate
4. extractionextracted with ethyl acetate/2-propanol
5. washThe obtained organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. washThe resulting solid was washed with ethyl acetate/methanol

ORD record

ord-42f2dd96e4534823840e5292aaace78d

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440987B2