Ammonium formate → (4-Fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine

HRID 475231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475231
[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:17]=[N:18]O.C([O-])=O.[NH4+]>CO.[Zn]>[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:17][NH2:18]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 866947334-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime

Produkt 1

HCID 86694734(4-Fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamineAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 150 (5.8 g, 0.022 mol) in MeOH (100 mL) was added zinc dust (2.9 g, 0.044 mol) and ammonium formate (2.8 g, 0.044 mol). The resulting mixture was heated to 75° C. for 2 h. The mixture was filtered through a Celite® pad. The filtrate was concentrated and the crude product was purified by SiO2 chromatography eluting with 5% MeOH/DCM to afford 2.6 g (47%) of (4-fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine (152) as a yellow solid: 1H-NMR (400 MHz, RT, CDCl3): δ 1.66-1.80 (m, 3H), 1.92-1.96 (m, 1H), 2.06-2.14 (m, 2H), 3.68-3.74 (m, 1H), 4.23-4.26 (m, 1H), 4.40 (br, 2H), 5.49-5.52 (dd, 1H), 6.94-6.99 (dd, 1H), 7.18-7.23 (t, 1H), and 7.37-7.39 (d, 1H); MS (ESI) m/z=250.2 [M+1]+.

Aufarbeitung

  1. filtrationThe mixture was filtered through a Celite® pad
  2. concentrationThe filtrate was concentrated
  3. customthe crude product was purified by SiO2 chromatography
  4. washeluting with 5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-7cc31387f4a1417bb5ceb9d19b2ef9da
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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