Dimethylformamide → ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate

HRID 420140노트

반응식

HRID 420140 반응식
[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([OH:18])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.[C:19]([O-])([O-])=O.[K+].[K+].CN(C=O)C.CI>CCOC(C)=O>[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:18][CH3:19])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57930939ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

생성물 1

HCID 66649481ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate수율 98.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a stirred suspension of 14.56 g of ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate and 16.2 g of K2CO3 and 220 ml of DMF was added 7.48 ml of MeI and the mixture was stirred at 60° C. for 3 hrs. The mixture was allowed to cool, diluted with EtOAc, washed with water and saturated brine successively, dried over Na2SO4, then concentrated. The residue was purified on SiO2 column chromatography (n-hexane-EtOAc) to afford 15.15 g of ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate as a pale yellow oil.

후처리

  1. temperatureto cool
  2. washwashed with water and saturated brine successively
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified on SiO2 column chromatography (n-hexane-EtOAc)

출처 및 근거

ORD 기록
ord-0eb400ffa6964be08a89773913045090
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093389B2

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