Ethyl Acetate → HCID 59366199, compound

HRID 532817Notes

Reaction equation

HRID 532817 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 59366199HCID 59366199, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-7116c240067a43088e267879a49b74c2
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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