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Ethyl Glycolate → Ethyl({2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}oxy)acetate

HRID 1512807
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1512807
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].CC1C=CC(S(O[CH2:21][CH2:22][C:23]2[C:31]3[C:26](=[C:27]([C:32]4[N:36]=[C:35]([C:37]5[CH:42]=[CH:41][C:40]([O:43][CH:44]([CH3:46])[CH3:45])=[C:39]([Cl:47])[CH:38]=5)[O:34][N:33]=4)[CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:48])[CH:24]=2)(=O)=O)=CC=1>CN(C=O)C>[Cl:47][C:39]1[CH:38]=[C:37]([C:35]2[O:34][N:33]=[C:32]([C:27]3[CH:28]=[CH:29][CH:30]=[C:31]4[C:26]=3[N:25]([CH3:48])[CH:24]=[C:23]4[CH2:22][CH2:21][O:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:36]=2)[CH:42]=[CH:41][C:40]=1[O:43][CH:44]([CH3:45])[CH3:46]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 591460252-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 59146091Ethyl({2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}oxy)acetateAusbeute 136,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a stirred solution of ethyl hydroxyacetate (23 mg) in DMF (5 mL) was added NaH (18 mg). The reaction mixture was stirred at 20° C. for 15 mins. Then a solution of 2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl 4-methylbenzenesulfonate (D127) (25 mg) in DMF was added dropwise. The mixture was stirred at room temperature for 24 h. The reaction was quenched with water, partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with water, 2 M hydrochloric acid and brine, dried over sodium sulphate and evaporated to give the crude product ethyl ({2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}oxy)acetate (D104) (30 mg), used directly in the next step. MS (ES): C26H28ClN3O5 requires 497; found 498.2 (M+H+).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 24 h
  2. customThe reaction was quenched with water
  3. custompartitioned between ethyl acetate (25 mL) and water (25 mL)
  4. washThe organic phase was washed with water, 2 M hydrochloric acid and brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-69e4b4a6f47b4f3caec925864f84cf5b
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217028B2

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