Реакция #84638

Уравнение реакции

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

Выход 84.8%

Растворители

1,4-dioxane water

Условия реакции

Обработка

1. 1
   Другоеwas degassed with nitrogen for 5 min
2. 2
   ТемператураThe reaction mixture was cooled to room temperature
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   Промывкаwashed with saturated ammonium chloride solution
5. 5
   Сушкаdried with sodium sulfate
6. 6
   ДругоеThe residue was purified by silica gel column chromatography

Методика

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]+.

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