HCID 66760614, compound → HCID 66760481, compound

HRID 889188Notes

Reaction equation

HRID 889188 reaction equation
C([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH2:18][CH3:19])[N:14]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH2:18]([C:15]1[N:14]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:8])[C:17]=2[N:16]=1)[CH3:19]

Participants

4

Reactant 1

HCID 66760614HCID 66760614, compound

Product 1

HCID 66760481HCID 66760481, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

To a solution cold solution (ice bath) of 7-benzyloxy-2-ethyl-1H-benzimidazole prepared above (0.8 g, 3.17 mmol) in DMF (10 mL) was added sodium hydride (0.41 g, 10.47 mmol), followed by 2-(bromomethyl)pyridine hydrobromide (0.88 g, 3.49 mmol). After addition of the bromide the reaction mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was partitioned between water and ethyl acetate. Ethyl acetate layer was separated, dried (MgSO4), and concentrated to give 4-benzyloxy-2-ethyl-1-pyridin2-ylmethyl-1H-benzoimidazole as a solid which was crystallized in ethyl acetate to give 4-benzyloxy-2-ethyl-1-pyridin2-ylmethyl-1H-benzoimidazole, 0.35 g. LCMS 344 (M+1). 1HNMR (400 MHz, CDCl3) δ 1.38 (t, 3H), 2.90 (q, 2H), 5.40-5.42 (m, 4H), 6.65-8.60 (12H, Ar) 4-benzyloxy-2-ethyl-1-pyridin2-ylmethyl-1H-benzoimidazole (0.35 g, 1.2 mmol) was dissolved in ethanol and in presence of Pd/C, 10% and stirred under a hydrogen balloon overnight. The solution was filtered through celite and concentrated to give 2-ethyl-1-pyridin-2-ylmethyl-1H-benzoimidazole-4-ol. 1HNMR (400 MHz, CDCl3) δ 1.28 (t, 3H), 2.87 (q, 2H), 5.40 (s, 2H), 6.49 (d, 1Har), 6.51 (m, 2H, Ar), 6.92 (m. 1H Ar), 7.09 (m, 1H, Ar), 7.73 (m, 1H, Ar), 8.49 (m, 1H, Ar), 9.57 (1H, OH).

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-75cfd7107e7449d7a9539b0be0fd2a2f
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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