Potassium Carbonate → 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

HRID 2212527

반응식

HRID 2212527 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)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:24][CH:25]=[CH:26][CH2:27][CH2:28]Br>CN(C=O)C.CCOCC.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:28][CH:27]=[CH:26][CH2:25][Br:24])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 10657398N-Boc-5-HydroxyindolineHCID 536293111,4-Dibromobut-1-ene

생성물 1

HCID 695150785-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester수율 31.9%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

514 mg (2.3 mmol) 5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 12 ml DMF were treated with 830 mg (6 mmol) powdered K2CO3 and 1070 mg (5 mmol) 1,4-dibromobutene. The suspension was stirred at 50° C. for 3 h, cooled to RT, diluted with ether and water. The aqueous phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with hexane/EtOAc 9:1 yielded 270 mg (31%) 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless solid, MS: 368 (MH+, 1Br).

후처리

  1. temperaturecooled to RT
  2. extractionThe aqueous phase was extracted with ether
  3. washthe organic phases were washed with water
  4. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-fa12095754984bc18bb2b8a6b6e67c0b
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102007B2

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