Potassium Phosphate, Tribasic → (E)-5-(2-(4-methoxyphenyl)prop-1-enyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401518
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.N1CCC[C@H]1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH:33]=[C:34]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)[CH3:35]>CN(C=O)C.[Cu]I>[CH3:43][O:42][C:39]1[CH:40]=[CH:41][C:36](/[C:34](/[CH3:35])=[CH:33]/[N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]3[CH2:3][N:2]([CH3:1])[CH2:15][CH2:14][C:5]2=3)=[CH:37][CH:38]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 854087261-(1-Bromoprop-1-en-2-yl)-4-methoxybenzene

Produkt 1

HCID 59455100(E)-5-(2-(4-methoxyphenyl)prop-1-enyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (36.7 mg, 0.184 mmol) was dissolved in DMF (6 mL). Copper (I) iodide (4 mg, 0.0184 mmol), L-proline (4.2 mg, 0.037 mmol) and potassium phosphate (78 mg, 0.37 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 1-(1-Bromoprop-1-en-2-yl)-4-methoxybenzene (50 mg, 0.22 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 80° C. (prolonged heating in some cases was required). DMF was evaporated under reduced pressure, the residue was diluted with water and the solid was filtered. The solid material was purified by silica gel chromatography (100-200 mesh). Yield: 45 mg. 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 7.60 (d, 2H), 7.25 (s, 1H), 7.10 (d, 1H), 7.0 (m, 4H), 4.30 (m, 2H), 3.80 (s, 3H), 3.50 (m, 2H), 2.98 (m, 2H), 2.85 (s, 3H), 2.38 (s, 3H), 1.80 (s, 3H).

Aufarbeitung

  1. customthe reaction mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated overnight at 80° C. (
  3. temperatureprolonged heating in some cases
  4. customDMF was evaporated under reduced pressure
  5. additionthe residue was diluted with water
  6. filtrationthe solid was filtered
  7. customThe solid material was purified by silica gel chromatography (100-200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-7d6c9f5f87ad43df9fc147e25a47b765
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907097B2

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