Benzyl iodide → HCID 22739195, Verbindung

HRID 51463

Reaktionsgleichung

Reaktionsgleichung von HRID 51463
[CH2:1]([N:8]1[CH2:20][C:19](=[O:21])[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:22]([O:24][CH3:25])=[O:23])[NH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:28](I)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1.C(Cl)Cl>[CH2:1]([N:8]1[CH2:20][C:19](=[O:21])[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:22]([O:24][CH3:25])=[O:23])[N:11]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 12098Benzyl iodideHCID 24758Sodium hydrideHCID 22740791HCID 22740791, Verbindung

Produkt 1

HCID 22739195HCID 22739195, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-benzyl-4-oxo-5-carbomethoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (0.928 g, 2.78 mmol) in dry tetrahydrofuran (5 mL) was added 60% sodium hydride in oil (111 mg). The resulting mixture was stirred at room temperature until gas evolution ceased. A solution of benzyl iodide (0.606. g, 2.78 mmol) in dry tetrahydrofuran (5 mL) was added to the reaction mixture and the resulting solution stirred at room temperature for 60 h. The mixture was diluted with methylene chloride and washed twice with saturated sodium chloride solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate resulting in a yellow precipitate (163 mg). The filtrate was concentrated in vacuo and chromatographed (silica gel, 5% methanol/95% methylene chloride) to provide an additional 580 mg of the title compound (743 mg total, 63%) as a crystalline solid: mp 198-199° C. 1H NMR (CDCl3) d 7.43 (d, J=7 Hz, 1 H), 7.36 (d, J=8 Hz, 1 H), 7.25 (m, 9 H), 6.95 (m, 2 H), 5.24 (s, 2 H), 4.01 (s, 3 H), 3.78 (m, 4 H), 3.40 (bs, 2 H); MS EI+ m/e 425 (p+1); IR (KBr, cm−1) 1726, 1648, 1449, 1291, 1134, 1107.

Aufarbeitung

  1. stirringthe resulting solution stirred at room temperature for 60 h
  2. washwashed twice with saturated sodium chloride solution
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate resulting in a yellow precipitate (163 mg)
  7. concentrationThe filtrate was concentrated in vacuo
  8. customchromatographed (silica gel, 5% methanol/95% methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-5fb86ef60f76460d83f83944d99e4b4f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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