Acetic Acid → HCID 58154281, compound

HRID 1619102Notes

Reaction equation

HRID 1619102 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][C:13](=[O:24])[N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:10][CH:9]=1.I[CH2:26][CH2:27][O:28][CH2:29][CH2:30]I.C(O)(=O)C>CN(C=O)C.O.C(OCC)(=O)C>[Br:7][C:8]1[CH:16]=[C:15]2[N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:13](=[O:24])[C:12]3([CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:11]2=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 34307792-Iodoethyl etherHCID 58154275tert-Butyl 6-bromo-2-oxoindoline-1-carboxylate

Product 1

HCID 58154281HCID 58154281, compoundYield 73.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (20.7 g, 63.5 mmol) was added portionwise over a 20 minute period to a stirred solution of tert-butyl 6-bromo-2-oxoindoline-1-carboxylate (preparation 8a, 6.0 g, 16.0 mmol) and 1-iodo-2-(2-iodoethoxy)ethane (6.58 g, 17.6 mmol) in N,N′-dimethylformamide (250 mL) at −20° C. under an argon atmosphere. After the addition the mixture was warmed to room temperature and stirred for 3 hours. Acetic acid (1.1 mL) followed by ethyl acetate and water were added to the reaction mixture and the organic layer was separated, washed with water, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (10:1 to 5:1 hexanes/ethyl acetate) gave the title compound (4.50 g, 61%) as a pale yellow solid.

Workup

  1. additionAfter the addition the mixture
  2. additionwere added to the reaction mixture
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification of the residue by flash chromatography (10:1 to 5:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-36f2481eb1d040969945856d40836e72
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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