1-Bromo-3-chloropropane → 5-(3-Chloro-propoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 901103

반응식

HRID 901103 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:17][CH2:18][CH2:19][Cl:20])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

생성물 1

HCID 451123565-(3-Chloro-propoxy)-1H-indole-2-carboxylic acid ethyl ester수율 74%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

반응 조건

온도
80 °C

실험 절차

To a solution of ethyl-5-hydroxyindole-2-carboxylate (15 g, 73 mmol, 1.0 eq.) and 1-bromo-3-chloropropane (8.8 mL, 88 mmol, 1.2 eq.) in 2-butanone (200 mL) was added potassium carbonate (12.1 g, 88 mmol, 1.2 eq.). The reaction mixture was stirred 160 h at 80° C. The reaction mixture was cooled down and partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and brine then dried over sodium sulfate, filtered and concentrated in vacuo. The crude mixture was purified by column chromatography on silica eluting with cyclohexane/ethyl acetate 9:1 to yield 15.3 mg (74%) of the title compound as a light yellow solid. MS (m/e): 282.7 (MH+, 100%).

후처리

  1. temperatureThe reaction mixture was cooled down
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by column chromatography on silica eluting with cyclohexane/ethyl acetate 9:1

출처 및 근거

ORD 기록
ord-891340eab47746c18ea2a6b9e9b1bd4d
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361682B2

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