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1,10-Phenanthroline → 8-chloro-2-methyl-5-((6-methylpyridin-3-yl)ethynyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401696
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1401696
[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.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[K+].[K+].Br[C:37]#[C:38][C:39]1[CH:40]=[CH:41][C:42]([CH3:45])=[N:43][CH:44]=1>C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:37]#[C:38][C:39]3[CH:44]=[N:43][C:42]([CH3:45])=[CH:41][CH:40]=3)[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 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 120404695-(2-Bromoethynyl)-2-methylpyridine

Produkt 1

HCID 594549138-chloro-2-methyl-5-((6-methylpyridin-3-yl)ethynyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

8-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (56 mg, 0.255 mmol) was dissolved in toluene and copper sulfate (6.3 mg. 0.0255 mmol) was added, followed by 1,10-phenanthroline (9.18 mg, 0.051 mmol) and potassium carbonate (70.38 mg, 0.51 mmol). 5-(Bromoethynyl)-2-methylpyridine (50 mg, 0.255 mmol) dissolved in toluene was added and the mixture purged with nitrogen in it. The reaction mixture was heated at 85° C. overnight. The reaction was monitored by TLC and LCMS. Toluene was concentrated under vacuum and the residue washed with water. The crude product was purified by column chromatography using 0-3% MeOH:DCM as eluent, to give the product as a yellow solid. 1H NMR (CDCl3, freebase) δ (ppm): 8.65 (s, 1H), 7.70 (d, 1H), 7.48 (d, 1H), 7.38 (s, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 3.60 (s, 2H), 2.96 (m, 2H), 2.80 (m, 2H), 2.60 (s, 3H), 2.56 (s, 3H).

Aufarbeitung

  1. additionwas added
  2. customthe mixture purged with nitrogen in it
  3. concentrationToluene was concentrated under vacuum
  4. washthe residue washed with water
  5. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f6a2f70fc484b7c9a8fdd8481f0bcbb
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08907097B2

Notizen zur Reaktion

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