Sodium hydride → HCID 49779378, Verbindung

HRID 1773287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773287
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([CH3:17])[CH2:14][CH2:13][C:9]=3[NH:10][C:11]=2[CH:12]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:20][C:21]1([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH2:23][O:22]1>CN(C=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([CH3:17])[CH2:14][CH2:13][C:9]=3[N:10]([CH2:20][C:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)([OH:22])[CH3:23])[C:11]=2[CH:12]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 123953864-(2-Methyloxiran-2-yl)pyridineHCID 66611743HCID 66611743, Verbindung

Produkt 1

HCID 49779378HCID 49779378, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7-isopropyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (500 mg, 2.1 mmol) in DMF (10 mL) was added sodium hydride (252 mg, 6.3 mmol). After stirring for 10 min at RT, 4-(2-methyl-oxiranyl)-pyridine (444 mg, 3.2 mmol) was added and stirring continued for another 16 h. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate and concentrated to afford crude product which was re-crystallized in ether and hexane to yield 1-(7-isopropyl-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-2-(pyridin-4-yl)propan-2-ol. 1H NMR (CD3OD, TFA salt) d (ppm): 8.60 (d, 2H), 8.05 (d, 2H), 7.25 (d, 1H), 6.90 (d, 1H), 6.78 (s, 1H), 4.65 (m, 1H), 4.42 (s, 2H), 4.30 (m, 1H), 3.90 (m, 1H), 3.60 (m, 2H), 3.30 (m, 1H), 3.10 (s, 3H), 2.85 (m, 1H), 1.80 (s, 3H), 1.18 (m, 6H).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for another 16 h
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford crude product which
  8. customwas re-crystallized in ether

Quellen und Nachweise

ORD-Eintrag
ord-a7dde935e5a6425e94e39902455a6d1d
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255094B2

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