Potassium Phosphate, Tribasic → (E)-2,3,8-trimethyl-5-(2-(6-methylpyridin-3-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401541
[CH3:1][N:2]1[CH:15]([CH3:16])[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:18]1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH:34]=[CH:35][C:36]1[CH:37]=[CH:38][C:39]([CH3:42])=[N:40][CH:41]=1>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH:15]([CH3:16])[CH2:14][C:5]2[N:6](/[CH:34]=[C:35](/[C:36]3[CH:41]=[N:40][C:39]([CH3:42])=[CH:38][CH:37]=3)\[CH3:18])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 666120872,3,8-Trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 722566695-(2-Bromovinyl)-2-methylpyridine

Produkt 1

HCID 53373125(E)-2,3,8-trimethyl-5-(2-(6-methylpyridin-3-yl)prop-1-enyl)-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

2,3,8-Trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (107 mg, 0.5 mmol) was dissolved in DMF. Copper (I) iodide (9.5 mg, 0.05 mmol), L-proline (11.5 mg, 0.1 mmol) and potassium phosphate (414 mg, 2 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 5-(2-bromovinyl)-2-methylpyridine (116 mg, 0.55 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 100° 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) eluting with 0-7% MeOH-DCM. Yield: 125 mg. 1H NMR (CD3OD, oxalate salt) δ (ppm): 8.78 (s, 1H), 8.22 (d, 1H), 7.90 (s, 1H), 7.58 (d, 1H), 7.30 (s, 1H), 7.18 (d, 1H), 7.10 (d, 1H), 4.60 (m, 2H), 4.0 (m, 1H), 3.30 (m, 1H), 3.05 (m, 3H), 2.95 (m, 1H), 2.65 (s, 3H), 2.42 (s, 3H), 2.0 (s, 3H), 1.50 (d, 3H).

Aufarbeitung

  1. customthe reaction mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated overnight at 100° 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)
  8. washeluting with 0-7% MeOH-DCM

Quellen und Nachweise

ORD-Eintrag
ord-155cd803d48540d286a7130e03dc4f12
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907097B2

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