Sodium hydride → HCID 58577477, compound

HRID 1044239Notes

Reaction equation

HRID 1044239 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[NH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]=1)(=[O:6])=[O:5].[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl.[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH3:3][S:4]([C:7]1[N:8]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:24])([CH3:23])[CH3:16])[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]=1)(=[O:5])=[O:6]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 5284359Calcium ChlorideHCID 178504837HCID 178504837, compound

Product 1

HCID 58577477HCID 58577477, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (122 mg) (60% in mineral oil) was added to a solution of 2-(methylsulfonyl)-1H-imidazo[4,5-c]pyridine (500 mg) and 2-(trimethylsilyl)ethoxymethyl chloride (0.538 mL) in DMF (3 ml) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The reaction mixture was diluted with MeOH (2 mL), and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane) to give 2-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazo[4,5-c]pyridine (330 mg) as a light brown solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-c2a032d899fe4ebaa971d73d5c76b7c0
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

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