Reaktion #89453

Reaktionsgleichung

2-(((2S,3R)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

5-fluoro-2-iodobenzoic acid

DIPEA

HATU

→

title compound

Ausbeute 62.4%

2-(((2S,3R)-1-(5-Fluoro-2-iodobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

Ausbeute 62.4%

Lösungsmittel

EtOAc

DMA

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 10% aq. LiCl (3×50 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by flash column chromatography on silica gel (0% to 70% EtOAc/hexanes)

Vorschrift

To a stirred solution of 2-(((2S,3R)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (440 mg, 1.70 mmol), 5-fluoro-2-iodobenzoic acid (543 mg, 2.04 mmol), and DIPEA (438 mg, 3.40 mmol) in anhydrous DMA (10 mL) was added HATU (971 mg, 2.55 mmol) at rt under nitrogen and the reaction stirred for 16 h. The reaction mixture was diluted with EtOAc (100 mL), washed with 10% aq. LiCl (3×50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (0% to 70% EtOAc/hexanes) to afford the title compound as a yellow oil (537 mg, 62%). ESI MS (M+H) 507.

Quelle