Dimethylformamide → HCID 58017142, compound

HRID 883666Notes

Reaction equation

HRID 883666 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[CH:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]1=[O:21])=[O:5])[CH3:2].CN(C)C=O.Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>O>[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[C:8]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]1=[O:21])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 79177tert-Butyl bromoacetateHCID 58017122HCID 58017122, compound

Product 1

HCID 58017142HCID 58017142, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of diethyl-5-chloro-2-oxoindoline-1,3-dicarboxylate, intermediate 50, (5.0 g, 16.04 mmol) in anhydrous N,N-dimethylformamide (80 ml) 1,8-diazabicyclo[5.4.0]undec-7-ene (2.63 ml, 17.64 mmol) was added dropwise at ambient temperature at such a rate that the internal temperature remained below 30° C. After continuous stirring at ambient temperature for one hour the solution was treated with tert-butyl bromoacetate (2.73 ml, 18.45 mmol) and stirring was allowed to continue for 72 h. Water (100 ml) was added, the product was extracted with tert-butyl methyl ether (2×50 ml), the combined extracts were washed with brine (50 ml) and dried (MgSO4) to give a red solid (7.11 g). Purification by flash chromatography (n-heptane/ethyl acetate=15%; increased up to 20%) yielded the title compound (4.00 g, 59%) as colorless solid (HPLC purity: 99%).MS (ESI+): 426.3

Workup

  1. customremained below 30° C
  2. stirringstirring
  3. waitto continue for 72 h
  4. extractionthe product was extracted with tert-butyl methyl ether (2×50 ml)
  5. washthe combined extracts were washed with brine (50 ml)
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-682114239103437abc2c4ddf67f80710
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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