Potassium Phosphate, Tribasic → HCID 53372996, Verbindung

HRID 1400463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400463
[F:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[C:6]3[CH2:14][N:13]([CH3:15])[CH2:12][CH2:11][C:7]=3[NH:8][C:9]=2[CH:10]=1.N1CCC[C@H]1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH:34]=[C:35]([C:37]1[CH:38]=[CH:39][C:40]([CH3:43])=[N:41][CH:42]=1)[CH3:36]>CN(C=O)C.[Cu]I>[F:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[C:6]3[CH2:14][N:13]([CH3:15])[CH2:12][CH2:11][C:7]=3[N:8](/[CH:34]=[C:35](/[C:37]3[CH:42]=[N:41][C:40]([CH3:43])=[CH:39][CH:38]=3)\[CH3:36])[C:9]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 67311268HCID 67311268, VerbindungHCID 866447585-(2-Bromo-1-methyl-vinyl)-2-methyl-pyridine

Produkt 1

HCID 53372996HCID 53372996, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

7,8-Difluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (177 mg, 0.8 mmol) was dissolved in DMF (5 mL). Copper (I) iodide (19 mg, 0.10 mmol), L-proline (23 mg, 0.20 mmol) and potassium phosphate (424 mg, 2 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 5-(1-Bromoprop-1-en-2-yl)-2-methylpyridine (212 mg, 1 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). The product was further purified by HPLC. 1H NMR (CDCl3, TFA salt) δ (ppm): 9.10 (s, 1H), 8.22 (d, 1H), 7.60 (d, 1H), 7.15 (t, 1H), 7.02 (s, 1H), 6.95 (t, 1H), 4.70 (m, 1H), 4.10 (m, 1H), 3.90 (m, 1H), 3.30 (m, 2H), 3.05 (s, 3H), 2.90 (m, 1H), 2.80 (s, 3H), 2.0 (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)
  8. customThe product was further purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a1451a2a2f984b95b3a6199262d848ab
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906925B2

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