Reaction #89845

Reaction equation

tert-butyl 2-bromoacetate

tert-butyl 5-(2-(3-hydroxyphenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

tert-butyl 2-bromoacetate

K2CO3

→

tert-Butyl 5-(2-(3-(2-tert-butoxy-2-oxoethoxy)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Solvents

DMF

Conditions

Workup

1. 1
   Temperatureheating at 80° C.
2. 2
   Temperatureto cool to RT
3. 3
   Concentrationconcentrated in vacuo
4. 4
   workup.ADDITIONDiluted with CH2Cl2
5. 5
   Extractionextracted with water (3×)
6. 6
   OtherDried under Na2SO4
7. 7
   Concentrationconcentrated in vacuo

Procedure

A mixture of tert-butyl 5-(2-(3-hydroxyphenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.800 g, 1.76 mmol), tert-butyl 2-bromoacetate (130 μL, 0.88 mmol) and K2CO3 (0.972 g, 7.04 mmol) in DMF (35 mL) was heated at 80° C. for 2 h. Upon which additional tert-butyl 2-bromoacetate (130 μL, 0.88 mmol) was added, heating at 80° C. was continued for a further 1.5 h. The mixture was allowed to cool to RT and concentrated in vacuo. Diluted with CH2Cl2 and extracted with water (3×). Dried under Na2SO4 and concentrated in vacuo to give tert-Butyl 5-(2-(3-(2-tert-butoxy-2-oxoethoxy)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate. (0.950 g, 1.68 mmol, 95%).

Source