Methyl bromoacetate → HCID 85827769, compound

HRID 642146Notes

Reaction equation

HRID 642146 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].C1CCN2C(=NCCC2)CC1.Br[CH2:25][C:26]([O:28][CH3:29])=[O:27]>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:6](=[O:11])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 886955-Iodoisatin

Product 1

HCID 85827769HCID 85827769, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of 5-iodo-1H-indole-2,3dione (10.0 g, 36.6 mmol) in anhydrous DMF (180 ml) were added DBU (8.2 mL, 54.9 mmol) and methyl bromoacetate (5.1 mL, 54.9 mmol). After stirring at rt for 45 min, the reaction mixture was quenched with water (600 mL) and HCl (1N, 100 mL). Extraction with EtOAc (3×500 mL), drying over MgSO4 and evaporation under vacuo gave a residue. Recrystallization from AcOEt 150 mL) gave the title compound as an orange powder (6.45 g, 51%) in 99.1% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customthe reaction mixture was quenched with water (600 mL) and HCl (1N, 100 mL)
  2. extractionExtraction with EtOAc (3×500 mL)
  3. dry with materialdrying over MgSO4 and evaporation under vacuo
  4. customgave a residue
  5. customRecrystallization from AcOEt 150 mL)

Sources & evidence

ORD record
ord-adefcf6d37944ac9b3bd441a380c3450
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…