Dimethylformamide → methyl 2-methyl-1H-indole-4-carboxylate

HRID 11405

Reaction equation

HRID 11405 reaction equation
C(OCCOC1C=CC(C([N:14]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:23]C(O)=O)[C:17]=3[CH:16]=[C:15]2[CH3:27])=O)=CC=1)CC.CN(C)[CH:32]=[O:33].C(N(CC)CC)C.[C]=[O:43]>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[CH3:32][O:33][C:23]([C:18]1[C:17]2[CH:16]=[C:15]([CH3:27])[NH:14][C:22]=2[CH:21]=[CH:20][CH:19]=1)=[O:43]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 219743831-(4-(2-Propyloxyethoxy)benzoyl)-2-methylindole-4-acetic AcidHCID 178418416HCID 178418416, compound

Product 1

HCID 11769304methyl 2-methyl-1H-indole-4-carboxylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methyl-4-trifluoromethanesulfoxyindole (6.32 g; prepared in Reference Example 1) in methanol (33.43 ml)-N,N-dimethylformamide (200 ml) was added triethylamine (6.3 ml) and tetrakis(triphenylphosphine)palladium (2.6 g). The inside of the vessel was replaced with carbon monoxide and the mixture was stirred at 60° C. overnight. After the reaction was completed, to the mixture was added water and ethyl acetate and then the mixture was extracted. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate) to give the title compound (4.29 g) having the following physical data.

Workup

  1. extractionthe mixture was extracted
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0da4b96c7f31489a97331b969fe85f03
Source dataset
uspto-grants-2006_08
Patent number
US07098234B2

Linked notes

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