1-Bromo-3-chloropropane → 5-(3-Chloro-propoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Ethyl Ester

HRID 1437685노트

반응식

HRID 1437685 반응식
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:15](C(OC(C)(C)C)=O)[C:9]2=[N:10][CH:11]=[C:12]([OH:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH2:32][Cl:33].[Cl-].[NH4+]>CC(=O)CC>[CH2:2]([O:3][C:4]([C:6]1[NH:15][C:9]2=[N:10][CH:11]=[C:12]([O:14][CH2:30][CH2:31][CH2:32][Cl:33])[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:1]

참가 물질

6

반응물 4

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 684243571H-Pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 2-ethyl ester

생성물 1

HCID 684233145-(3-Chloro-propoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Ethyl Ester수율 32.4%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

The suspension consistent of 0.5 g (2.4 mmol) 5-hydroxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (as prepared in WO 05/000849), 0.4 g (2.6 mmol) potassium carbonate and 0.29 ml (0.46 g, 2.9 mmol) 1-bromo-3-chloropropane in 10 ml 2-butanone was heated under reflux for 23 hours. The reaction mixture was poured on 10% aqueous ammonium chloride solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel with n-heptane:ethyl acetate (1:1 v/v) as eluant to give 0.22 g (32%) of the desired compound as a colorless solid.

후처리

  1. temperatureunder reflux for 23 hours
  2. extractionwas extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was flash-chromatographed on silica gel with n-heptane:ethyl acetate (1:1 v/v) as eluant

출처 및 근거

ORD 기록
ord-46a7a713c3f94c5a9ece1db084dd7095
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622466B2

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