Imidazole → HCID 18631020, compound

HRID 1059945Notes

Reaction equation

HRID 1059945 reaction equation
Br.[OH:2][C:3]1[C:4]([C:9]2[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O.C(OCC)(=O)C>[Si:23]([O:2][C:3]1[C:4]([C:9]2[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)=[N:5][CH:6]=[CH:7][CH:8]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18667586HCID 18667586, compound

Product 1

HCID 18631020HCID 18631020, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 3-(3-hydroxypyridin-2-yl)nitrobenzene hydrobromide (0.3 g) and imidazole (165 mg) in N,N-dimethylformamide (3 ml) was added tert-butyldimethylsilyl chloride (183 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-butyldimethylsilyloxypyridin-2-yl)nitrobenzene (332 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-16c17dd23824402dad9680c20b5779f7
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

Loading…