Imidazole → N-Methoxy-N-methyl-2-(4-tributylsilanyloxymethyl-phenyl)-isonicotinamide

HRID 1909018Notes

Reaction equation

HRID 1909018 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][N:20]=2)[C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])=[CH:5][CH:4]=1.N1[CH:25]=[CH:24]N=C1.C[C:27]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])C>ClCCl>[CH3:17][O:16][N:14]([CH3:15])[C:12](=[O:13])[C:11]1[CH:18]=[CH:19][N:20]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][O:1][Si:30]([CH2:27][CH2:29][CH2:24][CH3:25])([CH2:32][CH2:5][CH2:6][CH3:7])[CH2:31][CH2:2][CH2:3][CH3:4])=[CH:4][CH:5]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 866643442-(4-(hydroxymethyl)phenyl)-N-methoxy-N-methylisonicotinamide

Product 1

HCID 87339143N-Methoxy-N-methyl-2-(4-tributylsilanyloxymethyl-phenyl)-isonicotinamideYield 147.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-hydroxymethyl-phenyl)-N-methoxy-N-methyl-isonicotinamide (206 mg, 0.76 mmol) in dichloromethane (1.5 mL) was added imidazole (57 mg, 0.83 mmol) and TBSCl (126 mg, 0.83 mmol). After stirring for 5 hours, the mixture was partitioned between dichloromethane and water. The organic layer was dried (MgSO4), evaporated and the residue purified by SiO2 chromatography (eluting with 30-60% EtOAc/hexanes) to give the title compound (264 mg).

Workup

  1. customthe mixture was partitioned between dichloromethane and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customthe residue purified by SiO2 chromatography (eluting with 30-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-410cd4b517d04f8787f8a04e0c2cd43f
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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