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Formic Acid → 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazole-5-carbaldehyde

HRID 1796486
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1796486
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]#N)=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][CH:18]=2)[CH2:3][CH2:2]1.C(O)=[O:27]>[Ni]>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH:14]=[O:27])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][CH:18]=2)[CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 284Formic AcidHCID 221813091-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazole-5-carbonitrile

Produkt 1

HCID 221812871-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazole-5-carbaldehydeAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 935NickelKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazole-5-carbonitrile (0.049 g, 0.149 mmol) in 50% aqueous formic acid (1 mL) was added a catalytic amount of Raney nickel (50% suspension in water) and the resulting mixture was heated at 90° C. for 6 hours. The mixture was filtered through a short pad of diatomaceous earth and washed with EtOAc. The solvent was evaporated in vacuo and the residue was taken up into EtOAc (5 mL). The organic phase was washed with 1 N NaOH (2×2 mL) and brine (2 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (40% EtOAc/hexanes) to provide the title compound (0.041 g, 82%) as a white solid. 1H NMR (acetone-d6): δ 10.16 (s, 1H), 8.29 (s, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.34 (d, J=8.4 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 4.44 (s, 2H), 4.24 (d, J=6.4 Hz, 2H) 4.07 (q, J=6.8 Hz, 2H), 1.40 (t, J=7.0 Hz, 3H), 1.27–1.14 (m, 1H), 0.58–0.49 (m, 2H), 0.48–0.38 (m, 2H). MS (ESI) (M+H)+=335.

Aufarbeitung

  1. filtrationThe mixture was filtered through a short pad of diatomaceous earth
  2. washwashed with EtOAc
  3. customThe solvent was evaporated in vacuo
  4. washThe organic phase was washed with 1 N NaOH (2×2 mL) and brine (2 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography (40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6e8b00c322ea4867950844743ae1af09
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07030139B2

Notizen zur Reaktion

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