Sodium hydride → tert-butyl 2-bromo-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate

HRID 1714005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714005
[H-].[Na+].Br[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:9][C:10]1[NH:11][C:12]2[C:17]([C:18]=1[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[CH:16][CH:15]=[C:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:13]=2>>[Br:9][C:10]1[N:11]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:12]2[C:17]([C:18]=1[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[CH:16][CH:15]=[C:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:13]=2

Komponenten

4

Edukt 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 59750072tert-Butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate2×

Produkt 1

HCID 68511006tert-butyl 2-bromo-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylateAusbeute 80 %

Versuchsvorschrift

NaH (1.4 eq, 60% dispersion in mineral oil) was added to a solution of tert-butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate in DMF (from Step 5, 0.15 M) and the solution stirred at RT for 30 min. Then methyl bromoacetate (1.4 eq) was added and the mixture stirred at RT for 3 h. The solvent was removed in vacuo and the residue taken up in EtOAc. The organic phase was washed twice with aqueous HCl (0.5 N) and then brine. The organic phase was dried over Na2SO4, filtered and the solvent evaporated in vacuo. The residue was purified by crystallisation (EtOAc/PE) to afford the title compound (80%); MS (ES+) m/z 450 (M+H)+, m/z 452 (M+H)+.

Aufarbeitung

  1. stirringthe mixture stirred at RT for 3 h
  2. customThe solvent was removed in vacuo
  3. washThe organic phase was washed twice with aqueous HCl (0.5 N)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by crystallisation (EtOAc/PE)

Quellen und Nachweise

ORD-Eintrag
ord-98994e008d0144688176e863f998dfb6
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795247B2

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