反応 #89453

反応方程式

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

5-fluoro-2-iodobenzoic acid

DIPEA

HATU

→

title compound

収率 62.4%

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

収率 62.4%

溶媒

EtOAc

DMA

反応条件

後処理

1. 1
   洗浄washed with 10% aq. LiCl (3×50 mL)
2. 2
   乾燥dried over Na2SO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The residue was purified by flash column chromatography on silica gel (0% to 70% EtOAc/hexanes)

実験手順

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.

出典