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

HRID 351639Notes

Reaction equation

HRID 351639 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-4899b2e49b434b22983d9153a2bad3f9
Source dataset
uspto-grants-2004_06
Patent number
US06743793B2

Reaction notes

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