Water → 6-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine

HRID 2409049Notes

Reaction equation

HRID 2409049 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][CH:9]=[N:10][C:4]=2[CH:3]=1.[H-].[Na+].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.O>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:9]=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 218138956-Chloro-3H-imidazo(4,5-c)pyridine

Product 1

HCID 866898596-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridineYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-3H-imidazo[4,5-c]pyridine (3.50 g, 22.79 mmol) in THF (50 mL) at 0° C. was slowly added sodium hydride (60% dispersion in mineral oil, 1.82 g, 45.58 mmol) in several portions. After stirring at RT for 30 min, 1-(chloromethyl)-4-methoxybenzene (4.30 g, 27.48 mmol) was added and the mixture was stirred at RT for 2 h. The reaction mixture was poured into water (100 mL) and extracted with EtOAc (100 mL×2). The combined extracts were washed with water (100 mL) and brine (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by SiO2 chromatography eluting with hexane/EtOAc (1:1) to afford 5.0 g (80%) of 6-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine as a white solid. MS (ESI): m/z=274.2 [M+1]+.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at RT for 2 h
  3. extractionextracted with EtOAc (100 mL×2)
  4. washThe combined extracts were washed with water (100 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-55fef2f5ead1433592f0812abb40949c
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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