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Sodium hydride → tert-Butyl-4-((6-(5-(3-isopropyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl) pyridin-3-yl) oxy)piperidine-1-carboxylate

HRID 1468039
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1468039
[OH:1][N:2]=[C:3]([NH2:7])[CH:4]([CH3:6])[CH3:5].[H-].[Na+].C(O[C:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]3[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]3)=[CH:26][N:25]=1)[CH:19]=[CH:18]2)=O)C>C1COCC1>[C:40]([O:39][C:37]([N:34]1[CH2:33][CH2:32][CH:31]([O:30][C:27]2[CH:26]=[N:25][C:24]([N:20]3[C:21]4[C:17](=[CH:16][C:15]([C:13]5[O:1][N:2]=[C:3]([CH:4]([CH3:6])[CH3:5])[N:7]=5)=[CH:23][CH:22]=4)[CH:18]=[CH:19]3)=[CH:29][CH:28]=2)[CH2:36][CH2:35]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2794833N'-Hydroxy-2-methylpropanimidamideHCID 67617454Ethyl-1-(5-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)pyridin-2-yl)-1H-indole-5-carboxylate

Produkt 1

HCID 86696203tert-Butyl-4-((6-(5-(3-isopropyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl) pyridin-3-yl) oxy)piperidine-1-carboxylateAusbeute 22,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of N′-hydroxyisobutyrimidamide (0.10 g, 1.0 mmol) in dry THF (10 mL), NaH (0.078 g, 3.26 mmol) was added and stirred at 60° C. for 2 h. The reaction contents were brought to room temperature, Ethyl-1-(5-((1-(tert-butoxycarbonyl)piperidin-4-yl) oxy) pyridin-2-yl)-1H-indole-5-carboxylate (0.205 g, 0.440 mmol) was added and stirred at 60° C. for 3 h. The reaction was quenched by methanol at 0° C. and concentrated in vacuo. The resultant residue was dissolved with ethyl acetate and washed with water, the organic layer was separated, concentrated in vacuo and the resulting residue was purified by flash column chromatography to give the title compound (0.050 g, 10.16%).

Aufarbeitung

  1. customThe reaction contents
  2. customwere brought to room temperature
  3. stirringstirred at 60° C. for 3 h
  4. customThe reaction was quenched by methanol at 0° C.
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resultant residue was dissolved with ethyl acetate
  7. washwashed with water
  8. customthe organic layer was separated
  9. concentrationconcentrated in vacuo
  10. customthe resulting residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ad749111d6bf40018f909b945ab7139d
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000175B2

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