Sodium hydride → 1-[3-(Pyridin-2-ylmethoxymethyl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester

HRID 547590Notes

Reaction equation

HRID 547590 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=2)[CH:12]=1)=[O:7])[CH3:4].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]OS(C)(=O)=O>C1COCC1>[CH2:3]([O:5][C:6]([C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][CH2:27][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=3)[CH:14]=2)[CH:12]=1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22417657Methanesulfonic acid pyridin-2-ylmethyl esterHCID 578263591-(3-Hydroxymethyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 160453461-[3-(Pyridin-2-ylmethoxymethyl)-phenyl]-1H-imidazole-4-carboxylic acid ethyl esterYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of NaH (120 mg, 3 mmol, 60% in mineral oil) in dry THF (10 mL) at 0° C. under N2 atmosphere was added a solution of compound 7 (394 mg, 1.2 mmol) in dry THF (5 mL) and reaction mixture was allowed to stir for 30 min at room temperature. Compound 11 (300 mg, 1.2 mmol) in THF (2 mL) was then added and stirring was continued for 12 h at room temperature [reaction was followed by TLC]. Reaction mixture was quenched with water (5 mL), extracted with CH2Cl2 (40 mL), washed with brine, dried over Na2SO4 and concentrated. The crude mass was purified by column chromatography over silica gel using 10% methanol in chloroform as eluant to give 11a (110 mg, 28%) as pale yellow solid, mp 76.7-78.8° C.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 12 h at room temperature
  4. custom[reaction was followed by TLC]
  5. customReaction mixture
  6. customwas quenched with water (5 mL)
  7. extractionextracted with CH2Cl2 (40 mL)
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customThe crude mass was purified by column chromatography over silica gel using 10% methanol in chloroform as eluant

Sources & evidence

ORD record
ord-7887cf0a092a49fc9a0ce7ba93b72e2f
Source dataset
uspto-grants-2011_05
Patent number
US07939556B2

Reaction notes

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