Реакция #89453

Уравнение реакции

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

5-fluoro-2-iodobenzoic acid

DIPEA

HATU

→

title compound

Выход 62.4%

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

Выход 62.4%

Растворители

EtOAc

DMA

Условия реакции

Обработка

1. 1
   Промывкаwashed with 10% aq. LiCl (3×50 mL)
2. 2
   Сушкаdried over Na2SO4
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   ДругоеThe residue was purified by flash column chromatography on silica gel (0% to 70% EtOAc/hexanes)

Методика

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.

Источник