반응 #73416

반응 방정식

(5-tert-butyl-isoxazol-3-yl)-carbamic acid phenyl ester

[6-(4-fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl]-methyl-carbamic acid tert-butyl ester

NaH

→

title compound

{6-[1-(5-tert-Butyl-isoxazol-3-ylcarbamoyl)-4-fluoro-2-methyl-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-methyl-carbamic acid tert-butyl ester

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGstir for 18 h
2. 2
   기타The mixture is then quenched with saturated aqueous ammonium chloride
3. 3
   추출The aqueous phase is extracted with EtOAc (2×)
4. 4
   세척The combined organic layers are washed with brine
5. 5
   건조dried over anhydrous sodium sulphate
6. 6
   농축concentrated
7. 7
   기타purified by FCC (0-70% EtOAc/heptane)

실험 절차

To a solution of [6-(4-fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl]-methyl-carbamic acid tert-butyl ester (275 mg, 0.712 mmol) in THF (7 mL), NaH (85 mg, 2.13 mmol) is added under nitrogen at 0° C. The resulting mixture is stirred for 2 h. Then (5-tert-butyl-isoxazol-3-yl)-carbamic acid phenyl ester (370 mg, 1.42 mmol) is added to this mixture. The resulting mixture is allowed to warm to rt and stir for 18 h. The mixture is then quenched with saturated aqueous ammonium chloride. The aqueous phase is extracted with EtOAc (2×). The combined organic layers are washed with brine, dried over anhydrous sodium sulphate, concentrated and purified by FCC (0-70% EtOAc/heptane) to provide the title compound. MS (ESI) m/z 553.1 (M+1).

출처