Bromide ion → HCID 66760614, compound

HRID 889187Notes

Reaction equation

HRID 889187 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16]([CH2:18][CH3:19])=[N:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br.Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.[Br-]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]2[N:15]=[C:16]([CH2:18][CH3:19])[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 178437463HCID 178437463, compound

Product 1

HCID 66760614HCID 66760614, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customEthyl acetate layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e47709f5d56a48d4ba1298af37a6d732
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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