Imidazole → HCID 18667651, compound

HRID 1059951Notes

Reaction equation

HRID 1059951 reaction equation
Br.[OH:2][CH2:3][C:4]1[C:5]([C:10]2[CH:11]=[C:12]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:14][CH:15]=2)=[N:6][CH:7]=[CH:8][CH:9]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C)C=O.C(OCC)(=O)C>[Si:24]([O:2][CH2:3][C:4]1[C:5]([C:10]2[CH:11]=[C:12]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:14][CH:15]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18667496HCID 18667496, compound

Product 1

HCID 18667651HCID 18667651, compoundYield 131.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 3-(3-hydroxymethylpyridin-2-yl)-nitrobenzene hydrobromide (0.3 g) and imidazole (106 mg) in N,N-dimethylformamide (3 ml) was added tert-butyldimethylsilyl chloride (216 mg), and the mixture was stirred for 18 hours. The mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution and brine. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure to give 3-(3-tert-butyldimethylsilyloxymethylpyridin-2-yl)nitrobenzene (438 mg).

Workup

  1. washwashed with a saturated aqueous sodium hydrogencarbonate solution and brine
  2. dry with materialThe separated organic layer was dried over sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-101500c310704d3d911fee027308d244
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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