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Tributylamine → 1-(1,1-Dimethylethyl) 5-methyl 2,3-dihydro-1H-indole-1,5-dicarboxylate

HRID 1944542
Notes
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Reaction equation

HRID 1944542 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CCCC)CCCC)CCC.[C]=O>CO.C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:5][C:6]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7622Tributylamine2×HCID 21865438tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylateHCID 178418416HCID 178418416, compound

Product 1

HCID 98141901-(1,1-Dimethylethyl) 5-methyl 2,3-dihydro-1H-indole-1,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 178479804HCID 178479804, compound
Catalyst
HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (4.0 g, 13.5 mmol), tributylamine and bis-triphenylphosphinopalladium(II) chloride (0.65 g, 0.926 mmol) in methanol was sealed in a Parr pressure apparatus and pressurized with 600 psi of carbon monoxide. The solution was heated at 100° C. for one week. The vessel was cooled to room temperature and the gas vented. The solution was filtered, and the solvent was evaporated in vacuo. The residue was purified by flash chromatography, on silica gel eluted with 10-40% ethyl acetate in hexane to give the product mixed with tributylamine, 2.5 g (67%). The product was used without further purification in the subsequent step.

Workup

  1. temperatureThe vessel was cooled to room temperature
  2. filtrationThe solution was filtered
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by flash chromatography, on silica gel
  5. washeluted with 10-40% ethyl acetate in hexane
  6. customto give the product
  7. customThe product was used without further purification in the subsequent step

Sources & evidence

ORD record
ord-ca2a02af4bdd478aaacee58e36d270a7
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394828B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes