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

HRID 1773234ノート

反応式

HRID 1773234 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

HCID 1184524585-(((4-Propyl-3 (trifluoromethyl)phenyl)amino)-methyl)benzofuran-2-carbonitrile収率 69.2%

反応条件

温度
37.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c6029bee30d143ea874691a85101342c
出典データセット
uspto-grants-2016_02
特許番号
US09255093B2

反応ノート

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