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

HRID 11405

反応式

HRID 11405 の反応式
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]

参加物

9

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 219743831-(4-(2-Propyloxyethoxy)benzoyl)-2-methylindole-4-acetic AcidHCID 178418416HCID 178418416、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0da4b96c7f31489a97331b969fe85f03
出典データセット
uspto-grants-2006_08
特許番号
US07098234B2

関連ノート

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