Sodium hydride → HCID 58577478, compound

HRID 587494Notes

Reaction equation

HRID 587494 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[NH:15][C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=1)(=[O:6])=[O:5].Cl[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22].[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH3:3][S:4]([C:7]1[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:9]2[C:10]([N:15]=1)=[N:11][CH:12]=[CH:13][CH:14]=2)(=[O:5])=[O:6]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 5284359Calcium ChlorideHCID 178504836HCID 178504836, compound

Product 1

HCID 58577478HCID 58577478, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (146 mg) was added to a solution of 2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (600 mg) and [2-(chloromethoxy)ethyl]trimethylsilane (609 mg) 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-b]pyridine (250 mg) as light brown oil.

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-f8fc616e54c647639ee737248bebb38f
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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