Reference of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 46 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)- phenyl)-2-(2-(5-(methylsulfonamidomethyl)-1 ,3-dioxoisoindolin-2- yl)acetoxy)ethyl)pyridine 1 -oxide (Compound 254): Scheme 46 Step 1 : Preparation of 1 ,3-dioxoisoindoline-5-carbonitrile (249): A mixture of 5-bromoisoindoline-1 ,3-dione (2.5 g, 1 1 .06 mmol) and Pd(Ph3P)4 (1 .406 g, 1 .217 mmol) in DMF (50 ml) was accurately degassed with nitrogen, then Zn(CN)2 (1 .299 g, 1 1 .06 mmol) was added and the solution, splitted in 5 vials, was heated under microwave irradiation at 200C for 1 hour. A 3% aqueous solution of NH4OH (200 ml) was added and the organic phase was extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with brine (150 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by silica gel flash chromatography (100% DCM to DCM: MeOH = 99: 1 ) to afford 1 ,3-dioxoisoindoline-5-carbonitrile as (0.522 g, 3.03 mmol, 27.4% yield, MS/ESI+ 172.9 [MH] +).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindoline-1,3-dione, its application will become more common.
Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; CARZANIGA, Laura; LA PORTA, Elena; GUALA, Matilde; WO2013/57013; (2013); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem