Ethyl Acetate → HCID 59366199, 화합물

HRID 532817노트

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HRID 532817 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:12][CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].CC([O-])(C)C.[K+].CCOC(C)=O>COCCOC>[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][N:24]([C:2]2[CH:3]=[C:4]([CH2:12][CH3:13])[CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 19381206HCID 19381206, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 59366199HCID 59366199, 화합물수율 53.2%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
60 °C

실험 절차

A mixture of 8-bromo-6-ethylquinoline (1.3 g, 5.51 mmol, 1.04 equiv) and 1-(tert-butoxycarbonyl)homopiperazine (1.06 g, 1.0 equiv) in 5.5 mL of DME was degassed with compressed nitrogen gas for 5 minutes. To the mixture was added t-BuOK (0.83 g, 1.4 equiv). After degassing for another 2 minutes, allylchloro[1,3-(2,6-di-isopropylphenyl)imidazol-2-ylidene]palladium (II) (61 mg, 0.02 equiv) was added and the resulting mixture was heated at 60° C. overnight and cooled down to room temperature. EtOAc (˜70 mL) was added and the mixture was filtered through celite. The filtrate was washed with saturated aqueous NaHCO3 (70 mL) and brine (70 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel flash column chromatography using 5% to 20% EtOAc in hexane to afford the title compound (1.0 g). MS (ES) m/z 356.2 (M+H+).

후처리

  1. customwas degassed with compressed nitrogen gas for 5 minutes
  2. customAfter degassing for another 2 minutes
  3. temperaturecooled down to room temperature
  4. filtrationthe mixture was filtered through celite
  5. washThe filtrate was washed with saturated aqueous NaHCO3 (70 mL) and brine (70 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel flash column chromatography

출처 및 근거

ORD 기록
ord-7116c240067a43088e267879a49b74c2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853202B2

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