Sodium hydride → 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 82689Notes

Reaction equation

HRID 82689 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH2:12]([N:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][C:21]=2[CH3:23])[N:16]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:15]1=[O:31])[CH3:13].[H-].[Na+].[Cl-].[Cl-].[Ca+2].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:12]([N:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][C:21]=2[CH3:23])[N:16]([C:24]2[CH:29]=[CH:28][C:27]([O:30][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])=[CH:26][CH:25]=2)[C:15]1=[O:31])[CH3:13]

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 516892Sodium BicarbonateHCID 5284359Calcium ChlorideHCID 58577432HCID 58577432, compound

Product 1

HCID 585775691-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triisopropylsilyl chloride (2.384 mL) was added to a solution of 1-ethyl-3-(4-hydroxyphenyl)-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2 g) and NaH (0.594 g) in DMF (20 ml) at 20° C. The mixture was stirred at 20° C. under a dry atmosphere (CaCl2 tube) for 1 h. The mixture was poured into sat. NaHCO3 at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-25% EtOAc in hexane) to give 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (4.0 g) as light brown crystals.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-25% EtOAc in hexane)

Sources & evidence

ORD record
ord-d75d716e3a094256a25576d4fee6cefb
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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