Sodium cyanoborohydride → HCID 58852273, Verbindung

HRID 1716608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716608
[F:1][C:2]1[C:3]([CH3:17])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:6]=2[CH:16]=1.[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH:23]([CH:28]=O)[CH2:22]2.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[F:1][C:2]1[C:3]([CH3:17])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:28][CH:23]4[CH2:22][C:21]5[C:25](=[CH:26][CH:27]=[C:19]([F:18])[CH:20]=5)[CH2:24]4)[CH2:14][CH2:15]3)[C:6]=2[CH:16]=1

Komponenten

6

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 58852270HCID 58852270, VerbindungHCID 588523096-fluoro-5-methyl-1-piperidin-4-yl-1H-benzoimidazole

Produkt 1

HCID 58852273HCID 58852273, VerbindungAusbeute 24,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 6-fluoro-5-methyl-1-piperidin-4-yl-1H-benzoimidazole (70 mg, 0.300 mmol) and 5-fluoroindane-2-carbaldehyde (49 mg, 0.300 mmol) in CH3OH (4 mL) and acetic acid (0.2 mL) was stirred at rt for 15 minutes. NaCNBH3 (40 mg, 0.635 mmol) was added and then the reaction mixture was stirred for 1 hour. The solvent was removed and the residue was diluted with CH2Cl2. The organic layers were washed with saturated NaHCO3, brine, and dried over Na2SO4. The organic extracts were removed under the reduced pressure and the residue was purified by flash chromatography (5% CH3OH in CH2Cl2) to afford 6-fluoro-1-[1-(5-fluoro-indan-2-ylmethyl)-piperidin-4-yl]-5-methyl-1H-benzoimidazole (28 mg, 24%) as a white solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 1 hour
  2. customThe solvent was removed
  3. additionthe residue was diluted with CH2Cl2
  4. washThe organic layers were washed with saturated NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. customThe organic extracts were removed under the reduced pressure
  7. customthe residue was purified by flash chromatography (5% CH3OH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-fb4028b2645442c293236945f67d43eb
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803816B2

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