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Potassium Phosphate, Tribasic → HCID 59455199, Verbindung

HRID 1401560
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1401560
[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: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>[CH3:36][C:35]([CH3:38])([CH3:37])/[C:34](/[C:39]1[CH:40]=[CH:41][N:42]=[CH:43][CH:44]=1)=[CH:33]\[N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:15][CH2:14][C:5]1=2
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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 86644760HCID 86644760, Verbindung

Produkt 1

HCID 59455199HCID 59455199, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

2,3,4,5-Tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (30 mg, 0.15 mmol) was dissolved in DMF. Copper (I) iodide, L-proline (4 mg, 0.03 mmol) and potassium phosphate (63 mg, 0.29 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 4-(1-bromo-3,3-dimethylbut-1-en-2-yl)pyridine (43 mg, 0.18 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 85° 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. The product was further purified by HPLC. 1H NMR (CD3OD, freebase) δ (ppm): 8.21 (d, 2H), 7.15 (m, 3H), 7.05 (s, 1H), 6.94 (d, 1H), 6.80 (s, 1H), 3.90 (s, 2H), 3.18 (t, 2H), 2.90 (t, 2H), 2.70 (s, 3H), 2.36 (s, 3H), 1.30 (s, 9H).

Aufarbeitung

  1. customthe reaction mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated overnight at 85° 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
  9. customThe product was further purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bb67e13bf697481bac231272dac7b593
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08907097B2

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