Triethylamine → 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carbonitrile

HRID 1467986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467986
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[N:19]=[CH:18][C:17]([O:20][CH:21]3[CH2:26][CH2:25][N:24]([C:27](OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[CH:16][CH:15]=1)[CH:9]=[CH:8]2)(=[O:4])=[O:3].C([N:36](CC)CC)C.N#CBr>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[N:19]=[CH:18][C:17]([O:20][CH:21]3[CH2:26][CH2:25][N:24]([C:27]#[N:36])[CH2:23][CH2:22]3)=[CH:16][CH:15]=1)[CH:9]=[CH:8]2)(=[O:3])=[O:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 67805679tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carboxylate

Produkt 1

HCID 866961864-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carbonitrileAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)-piperidine-1-carboxylate (0.3 g, 0.63 mmol) in dichloromethane (5 mL) trifluoroacetic acid (2.0 mL) was added at 0° C. and stirred at room temperature for 2-3 h. The solvent was removed in vacuo and the resulting residue was dissolved in dichloromethane (5 mL), triethylamine (0.193 g, 1.91 mmol) and the cyanogen bromide (0.101 g, 0.95 mmol) were added at 0° C. and stirred at room temperature for 2-3 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carbonitrile (0.160 g, 63%); MS: 397 (M+1).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resulting residue was dissolved in dichloromethane (5 mL)
  3. stirringstirred at room temperature for 2-3 h
  4. customThe reaction was quenched with water
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated in vacuo
  7. customthe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b9d76fd29eea40158672905b73f5b673
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000175B2

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