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

HRID 1773234

Reaktionsgleichung

Reaktionsgleichung von HRID 1773234
[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. The mixture was then 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 then 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-c6029bee30d143ea874691a85101342c
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255093B2

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