5-Bromo-2,3-dihydro-isoindol-1-one

Chemical Properties

Pink Solid

Uses

5-Bromoisoindolin-1-one was one of the reagents in discovering a new, selective 3-aminopyrazole based MK2-inhibitors.

Synthesis

The general procedure for the synthesis of 5-bromo-2,3-dihydroisoindol-1-one from 4-bromo-2-bromomethylbenzoic acid methyl ester was as follows: 4-bromo-2-bromomethylbenzoic acid methyl ester (3.70 g) was suspended in a methanol solution of 2 M ammonia (36 mL) and concentrated ammonium hydroxide (12 mL) and the reaction was carried out for 18 hours. After completion of the reaction, the solid product was collected by filtration to afford 5-bromo-2,3-dihydroisoindol-1-one as a colorless solid (2.3 g, 90% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.68 (m, 3H), 4.44 (s, 2H).

References

[1] Patent: WO2006/20879, 2006, A1. Location in patent: Page/Page column 66-67
[2] Patent: WO2015/52264, 2015, A1. Location in patent: Paragraph 0637; 0638
[3] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 121
[4] Patent: WO2005/73205, 2005, A1. Location in patent: Page/Page column 25
[5] Patent: US2007/49603, 2007, A1. Location in patent: Page/Page column 91-92