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8-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indole → HCID 59455064, Verbindung

HRID 1400643
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400643
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.Br[CH:33]=[C:34]([C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1)[C:35]([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:33]=[C:34](/[C:39]3[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=3)\[C:35]([CH3:38])([CH3:36])[CH3:37])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1
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Komponenten

7

Edukt 4

HCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 86644760HCID 86644760, Verbindung

Produkt 1

HCID 59455064HCID 59455064, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

8-Chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (220 mg, 1 mmol) was dissolved in DMF (3 mL). Potassium phosphate (424 mg, 2 mmol), copper (I) iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol) were added. A solution of 4-(1-bromo-3,3-dimethylbut-1-en-2-yl)pyridine (294 mg, 1.5 mmol) in DMF (2 mL) was added dropwise, the reaction mixture was purged with nitrogen, and heated at 85° C. overnight. The DMF was evaporated under reduced pressure and the reaction mixture was diluted with water. The resultant precipitate was filtered and purified by silica gel chromatography (100-200 mesh) using 0-8% MeOH:DCM as eluant. The compound was further purified by HPLC. Yield: 77.03 mg. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.30 (d, 2H), 7.30 (m, 4H), 7.18 (d, 1H), 6.90 (s, 1H), 4.50 (m, 1H), 4.20 (m, 1H), 3.80 (m, 1H), 3.50 (m, 1H), 3.15 (m, 2H), 3.05 (s, 3H), 1.35 (s, 9H).

Aufarbeitung

  1. customthe reaction mixture was purged with nitrogen
  2. customThe DMF was evaporated under reduced pressure
  3. additionthe reaction mixture was diluted with water
  4. filtrationThe resultant precipitate was filtered
  5. custompurified by silica gel chromatography (100-200 mesh)
  6. customThe compound was further purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7ec88cea5a504a1d9c98e8dbac286ebb
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906925B2

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