1,4-Dibromobutane → 5-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl ester

HRID 1633626노트

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HRID 1633626 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:28][CH2:27][CH2:26][CH2:25][Br:24])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 22596220N-Boc-5-Hydroxyindole

생성물 1

HCID 695484135-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl ester수율 75.2%

시약·촉매·용매 1

HCID 180Acetone용매2회

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온도
100 °C

실험 절차

6.07 g (26 mmol) 5-Hydroxy-indole-1-carboxylic acid tert-butyl ester in 10 ml acetone were treated with 13.8 g (100 mmol) powdered K2CO3 and 11.8 ml (100 mmol) 1,4-dibromobutane. The suspension was stirred at 100° C. for 3 h, cooled to RT, and acetone was added. The suspension was filtered and concentrated. The residue was redissolved in ether and 0.5 M HCl, the inorganic phase was extracted with ether and the combined organic phases were washed with water, and dried over Na2SO4. Column chromatography on silica gel with a gradient hexane to hexane/EtOAc 19:1 yielded 7.2 g (65%, 3 steps) 5-(4-Bromo-butoxy)-indole-1-carboxylic acid tert-butyl ester as colorless oil, MS: 367 (M, 1Br).

후처리

  1. temperaturecooled to RT
  2. filtrationThe suspension was filtered
  3. concentrationconcentrated
  4. dissolutionThe residue was redissolved in ether
  5. extraction0.5 M HCl, the inorganic phase was extracted with ether
  6. washthe combined organic phases were washed with water
  7. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-b1c2d94478784747b6f341c3eabbac13
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503907B2

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