Réaction #84638

Équation de réaction

tert-butyl ((1S,2R)-2-((6-bromoquinazolin-2-yl)amino)cyclopentyl)carbamate

(2-chloro-3-ethoxy-6-fluorophenyl)boronic acid

potassium phosphate

→

tert-butyl ((1S,2R)-2-((6-(2-chloro-3-ethoxy-6-fluorophenyl)quinazolin-2-yl)amino)cyclopentyl)carbamate

Rendement 84.8%

Solvants

1,4-dioxane water

Conditions de réaction

Traitement

1. 1
   Autrewas degassed with nitrogen for 5 min
2. 2
   TempératureThe reaction mixture was cooled to room temperature
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   Lavagewashed with saturated ammonium chloride solution
5. 5
   Séchagedried with sodium sulfate
6. 6
   AutreThe residue was purified by silica gel column chromatography

Mode opératoire

A mixture of tert-butyl ((1S,2R)-2-((6-bromoquinazolin-2-yl)amino)cyclopentyl)carbamate (50 mg, 0.12 mmol), (2-chloro-3-ethoxy-6-fluorophenyl)boronic acid (40 mg, 0.18 mmol), Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (4 mg, 0.005 mmol) and potassium phosphate (78 mg, 0.37 mmol) in 1,4-dioxane/water (1.15 mL/0.15 mL) was degassed with nitrogen for 5 min and stirred at 100° C. for 30 min under microwave. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with saturated ammonium chloride solution and dried with sodium sulfate. The residue was purified by silica gel column chromatography to afford tert-butyl ((1S,2R)-2-((6-(2-chloro-3-ethoxy-6-fluorophenyl)quinazolin-2-yl)amino)cyclopentyl)carbamate (51 mg, 83%). MS (ES+) C26H30ClFN4O3 requires: 500, found: 501 [M+H]+.

Source