Ethyl Acetate → HCID 59366199、化合物

HRID 532817ノート

反応式

HRID 532817 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 59366199HCID 59366199、化合物収率 53.2%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
60 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-7116c240067a43088e267879a49b74c2
出典データセット
uspto-grants-2014_10
特許番号
US08853202B2

反応ノート

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