Sodium hydride → 7,10-Dichloro-1,2,3,4,5,6-hexahydro-3-methyl-6-(2-(6-methylpyridin-3-yl)ethyl)azepino[4,5-b]indole

HRID 1469578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469578
[Cl:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:7]=3[C:6]=2[C:5]([Cl:17])=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:31][CH2:32][C:33]2[CH:34]=[N:35][C:36]([CH3:39])=[CH:37][CH:38]=2)(=O)=O)=CC=1>CN(C=O)C>[Cl:1][C:2]1[C:10]2[N:9]([CH2:31][CH2:32][C:33]3[CH:34]=[N:35][C:36]([CH3:39])=[CH:37][CH:38]=3)[C:8]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:7]=3[C:6]=2[C:5]([Cl:17])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 682839377,10-Dichloro-1,2,3,4,5,6-hexahydro-3-methylazepino[4,5-b]indoleHCID 866581512-(6-Methylpyridin-3-yl)ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 710076037,10-Dichloro-1,2,3,4,5,6-hexahydro-3-methyl-6-(2-(6-methylpyridin-3-yl)ethyl)azepino[4,5-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 7,10-dichloro-1,2,3,4,5,6-hexahydro-3-methylazepino[4,5-b]indole (200 mg, 0.746 mmol) in DMF (2 mL), sodium hydride (90 mg, 2.25 mmol) was added. After stirring at 60° C. for 30 min., 2-(6-methylpyridin-3-yl)ethyl 4-methylbenzenesulfonate (543 mg, 1.86 mmol) was added to the reaction mixture and the reaction mixture was stirred at the same temperature for 40 min. The progress of reaction was monitored by TLC and LCMS. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain the residue that was purified by reverse phase HPLC to obtain 7,10-dichloro-1,2,3,4,5,6-hexahydro-3-methyl-6-(2-(6-methylpyridin-3-yl)ethyl)azepino[4,5-b]indole. 1H NMR TFA: —CD3OD: 8.4 (s, 1H), 8.1 (d, 1H), 7.75 (d, 1H), 7.0 (q, 2H), 4.8 (m, 1H), 4.0 (m, 1H), 3.8 (m, 2H), 3.4 (m, 3H), 3.3 (m, 2H), 3.2 (t, 3H), 3.0 (s, 3H), 2.7 (s, 3H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at the same temperature for 40 min
  2. customThe progress of reaction
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto obtain the residue that
  9. customwas purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b83c8976412848e1a0d9bc0511eb7760
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006263B2

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