N,N-二甲基甲酰胺 → 2-甲基-1H-吲哚-4-甲酸 甲酯

HRID 11405

反应方程式

HRID 11405 反应方程式
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]

参与物

9

反应物 4

HCID 6228N,N-二甲基甲酰胺HCID 8471三乙胺HCID 219743831-(4-(2-Propyloxyethoxy)benzoyl)-2-methylindole-4-acetic AcidHCID 178418416HCID 178418416，化合物

产物 1

HCID 117693042-甲基-1H-吲哚-4-甲酸 甲酯

试剂、催化剂与溶剂 4

HCID 178418397HCID 178418397，化合物催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
60 °C

实验过程

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.

后处理

  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)

来源与证据

ORD记录
ord-0da4b96c7f31489a97331b969fe85f03
来源数据集
uspto-grants-2006_08
专利号
US07098234B2

关联笔记

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