Potassium Phosphate, Tribasic → (E)-7-chloro-5-(2-(4-fluorophenyl)prop-1-enyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401509
[Cl:1][C:2]1[CH:3]=[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:33]=[C:34]([C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[CH3:35]>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:14][N:13]([CH3:15])[CH2:12][CH2:11][C:7]=3[N:8](/[CH:33]=[C:34](/[C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)\[CH3:35])[C:9]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 666118837-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 86644757(1-Bromoprop-1-en-2-yl)-4-fluorobenzene

Produkt 1

HCID 59455268(E)-7-chloro-5-(2-(4-fluorophenyl)prop-1-enyl)-2-methyl-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

7-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (220 mg, 0.90 mmol) was dissolved in DMF (5 mL). Copper (I) iodide (17 mg, 0.09 mmol), L-proline (20 mg, 0.18 mmol) and potassium phosphate (380 mg, 1.8 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 1-(1-Bromoprop-1-en-2-yl)-4-fluorobenzene (230 mg, 1.09 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). 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 7.78 (m, 2H), 7.52 (d, 1H), 7.30 (m, 3H), 7.16 (d, 1H), 7.10 (s, 1H), 4.30 (m, 2H), 3.0 (s, 3H), 2.82 (m, 4H), 1.85 (s, 3H).

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)

Quellen und Nachweise

ORD-Eintrag
ord-293c5d2204ec47d2a3c5c7f98b125811
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907097B2

Notizen zur Reaktion

Wird geladen…