Reaktion #73416

Reaktionsgleichung

(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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstir for 18 h
2. 2
   SonstigeThe mixture is then quenched with saturated aqueous ammonium chloride
3. 3
   ExtraktionThe aqueous phase is extracted with EtOAc (2×)
4. 4
   WaschenThe combined organic layers are washed with brine
5. 5
   Trocknendried over anhydrous sodium sulphate
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified by FCC (0-70% EtOAc/heptane)

Vorschrift

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).

Quelle