Reaktion #71304

Reaktionsgleichung

HCl

2,2,2-trifluoro-N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)acetamide

diborane

→

(1-((1-(2,2,2-Trifluoroethylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe whole heated
2. 2
   Temperaturto reflux for 6 h
3. 3
   workup.WAITleft
4. 4
   Wascheneluted with 2N NH3/MeOH
5. 5
   SonstigeAfter evaporation
6. 6
   Sonstigethe residue was further purified by prep LCMS
7. 7
   Sonstigeto give a clear film (11 mg, 0.028 mmol, 16.3%)

Vorschrift

To a solution of 2,2,2-trifluoro-N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)acetamide (0.172 mmol, 70 mg) in THF (2 mL) was added diborane (1.719 mmol, 1.719 mL) and the whole heated to reflux for 6 h. The reaction mixture was allowed to cool to room temperature before being treated with 2N HCl (3 mL) and left to stand overnight. After this time the crude mixture was applied to an SCX column & eluted with 2N NH3/MeOH. After evaporation, the residue was further purified by prep LCMS to give a clear film (11 mg, 0.028 mmol, 16.3%). MS (ESI): m/z [M+H]+ 394.1.

Quelle