Sodium borohydride → 5-(((4-Propyl-3 (trifluoromethyl)phenyl)amino)-methyl)benzofuran-2-carbonitrile

HRID 1773229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773229
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]#[N:12])=[CH:8][C:7]=2[CH:13]=1)=O.[CH2:14]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[C:24]([F:27])([F:26])[F:25])[CH2:15][CH3:16].[BH4-].[Na+]>>[CH2:14]([C:17]1[CH:23]=[CH:22][C:20]([NH:21][CH2:1][C:3]2[CH:4]=[CH:5][C:6]3[O:10][C:9]([C:11]#[N:12])=[CH:8][C:7]=3[CH:13]=2)=[CH:19][C:18]=1[C:24]([F:25])([F:26])[F:27])[CH2:15][CH3:16]

Komponenten

4

Edukt 3

HCID 4311764Sodium borohydrideHCID 215337204-Propyl-3-(trifluoromethyl)anilineHCID 498318215-Formylbenzofuran-2-carbonitrile

Produkt 1

HCID 1184524585-(((4-Propyl-3 (trifluoromethyl)phenyl)amino)-methyl)benzofuran-2-carbonitrileAusbeute 69,2 %

Reaktionsbedingungen

Temperatur
37.5 °C

Versuchsvorschrift

5-Formylbenzofuran-2-carbonitrile (168 mg, 0.98 mmol) was added to 2 mL of TFE and stirred at 35-40° C. After 5 min, the solution became clear, 4-propyl-3-(trifluoromethyl)aniline (199 mg, 0.982 mmol) was added, and a yellow precipitate formed. The mixture was vigorously stirred at the same temperature for 0.5 hr, NaBH4 (44.6 mg, 1.18 mmol) was added and the reaction was stirred at this temperature for another 0.5 hr. LCMS indicated the reaction was complete, the mixture was filtered, and the residue was washed with TFE (2 mL). The solvent was concentrated under reduced pressure and the crude product was purified by silica gel flash chromatography, 100% Heptane-10% Ethyl Acetate/90% Heptane, to give 5-(((4-propyl-3 (trifluoromethyl)phenyl)amino)-methyl)benzofuran-2-carbonitrile (243 mg). LCMS retention time=1.76 minutes (LC method 3); MS (m+1)=358.8. 1H NMR (400 MHz, DMSO-d6) δ 0.88 (t, J=7.3 Hz, 3H), 1.48 (sxt, J=7.5 Hz, 2H), 2.47 (br. s., 2H) 4.41 (d, J=6.0 Hz, 2H), 6.64 (t, J=6.1 Hz, 1H), 6.74 (dd, J=8.4, 2.4 Hz, 1H), 6.86 (d, J=2.5 Hz, 1H), 7.10 (d, J=8.4 Hz, 1H), 7.59 (dd, J=8.7, 1.7 Hz, 1H), 7.71 (d, J=8.7 Hz, 1H), 7.78 (d, J=1.0 Hz, 1H), 8.09 (d, J=0.9 Hz, 1H).

Aufarbeitung

  1. customa yellow precipitate formed
  2. stirringThe mixture was vigorously stirred at the same temperature for 0.5 hr
  3. stirringthe reaction was stirred at this temperature for another 0.5 hr
  4. filtrationthe mixture was filtered
  5. washthe residue was washed with TFE (2 mL)
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe crude product was purified by silica gel flash chromatography, 100% Heptane-10% Ethyl Acetate/90% Heptane

Quellen und Nachweise

ORD-Eintrag
ord-a5a95282c732438f93b2aa3dde8d9f08
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255093B2

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