Imidazole → 2-[6-(tert-Butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenylamine
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=2[CH2:11]1.N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C)C=O>[Si:26]([O:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH:10]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[NH2:1])[CH2:19][CH2:18]2)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol (850 mg) in N,N-dimethylformamide (10 ml) were sequentially added imidazole (500 mg) and tert-butyldimethylsilyl chloride (480 mg), and the solution was stirred for 1 hour at room temperature. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (805 mg).
Workup
- extractionThe solution was extracted with ethyl acetate
- washsequentially washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated in vacuo
- customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)
Sources & evidence
- ORD record
- ord-2ed0ccce5f784e34967f1ce197c267d2
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612114B2
Reaction notes
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