Dichloromethane → Methyl 2-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)propanoate

HRID 404037Notes

Reaction equation

HRID 404037 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[C:8]2=[O:11])=[CH:4][CH:3]=1.[N+:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([O-:21])=[O:20].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:17][C:12]([N:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:2]([C:25]3[CH:26]=[CH:27][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=3)=[CH:3][CH:4]=2)[C:8]1=[O:11])([CH3:18])[C:13]([O:15][CH3:16])=[O:14]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 67306213Methyl 2-(6-bromo-1-oxoisoindolin-2-yl)-2-methylpropanoate

Product 1

HCID 67306803Methyl 2-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)propanoateYield 95%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
82.5 °C

Procedure

The compound of example 338 (2.4 g, 0.0076 mol), (4-nitrophenyl)boronic acid (1.649 g, 0.0098 mol) and Pd(dppf)Cl2: CH2Cl2 (0.186 g, 0.00022 mol) were taken in DMF (60 mL) under an argon atmosphere. To this reaction mixture, 2M solution of Na2CO3 (2.33 g, 0.022 mol, 10.99 mL) was added and the reaction mixture was stirred at 80 to 85° C. for 1 to 1.5 h. After completion of the reaction, water was added to the reaction mixture and the product obtained was extracted with diethyl ether. The combined ether layers were washed with water and brine, dried over anhydrous Na2SO4. The solvent was evaporated and the product was purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether) to afford the title compound.

Workup

  1. additionwas added to the reaction mixture
  2. customthe product obtained
  3. extractionwas extracted with diethyl ether
  4. washThe combined ether layers were washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was evaporated
  7. customthe product was purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-2d33c35c8b764fd5a5cf80896b54970a
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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