Reacción #88654

Ecuación de reacción

sodium hydroxide

Boric acid triisopropyl ester

2-cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine

n-butyllithium

→

title compound

(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)boronic acid

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at −78° C. for 30 min
2. 2
   workup.WAITat room temperature for 3 hr
3. 3
   Lavadowashed with ethyl acetate
4. 4
   Extracciónextracted with ethyl acetate/2-propanol
5. 5
   LavadoThe obtained organic layer was washed with brine
6. 6
   Secadodried over magnesium sulfate
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   LavadoThe resulting solid was washed with ethyl acetate/methanol

Procedimiento

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.

Fuente