Dichloromethane → (S)-Methyl 3-methyl-2-(6-(5-nitropyridin-2-yl)-1-oxoisoindolin-2-yl)butanoate

HRID 403983Notes

Reaction equation

HRID 403983 reaction equation
[CH3:1][CH:2]([CH3:27])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12](B3OC(C)(C)C(C)(C)O3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5].Br[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][N:30]=1.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>[CH3:27][CH:2]([CH3:1])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][N:30]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 123866646(S)-Methyl 3-methyl-2-(1-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-2-yl)butanoate

Product 1

HCID 131731547(S)-Methyl 3-methyl-2-(6-(5-nitropyridin-2-yl)-1-oxoisoindolin-2-yl)butanoate

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 390 (3 g, 0.0084 mol), 2-bromo-5-nitropyridine (1.95 g, 0.0096 mol) and Pd(dppf)Cl2: CH2Cl2 (0.196 g, 0.00024 mol) were taken in DMF (100 mL) under an argon atmosphere. To this reaction mixture, 2M solution of Na2CO3 (2.55 mg, 0.0241 mmol, 12 mL) was added. The reaction mixture was stirred at 80-85° C. for 1 to 1.5 h. After completion of the reaction, water was added and the product obtained was extracted with ether. The combined ether layers were washed with brine and dried over anhydrous Na2SO4 or anhydrous MgSO4. The solvent was evaporated and the product obtained was purified by flash chromatography to obtain the title compound

Workup

  1. additionwas added
  2. customthe product obtained
  3. extractionwas extracted with ether
  4. washThe combined ether layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4 or anhydrous MgSO4
  6. customThe solvent was evaporated
  7. customthe product obtained
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-bbbd7317a500415a94e397e0f998e5fb
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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