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

HRID 11405

반응식

HRID 11405 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0da4b96c7f31489a97331b969fe85f03
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098234B2

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