[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine → 1-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole
Reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]#[C:23][CH:24]2[CH2:26][CH2:25]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CN(C)C=O.[Cu]I>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([N:15]2[C:16]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:22]=[C:23]2[CH:24]2[CH2:25][CH2:26]2)[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of [4-(tert-butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine (3.84 g, 10.4 mmol) in N,N-dimethylformamide (60 mL) was added copper(I) iodide (100 mg, 0.525 mmol). After the reaction was refluxed for 48 hours, it was allowed to cool to room temperature, and the solvent was removed in vacuo. The residue was partitioned between water and dichloromethane. The dichloromethane was dried (MgSO4) and concentrated to give a dark residue that was used in the next step with no further purification. LC-MS (C23H35NOSi calc'd 369) m/z 370 (M+H).
Workup
- temperatureAfter the reaction was refluxed for 48 hours
- customthe solvent was removed in vacuo
- customThe residue was partitioned between water and dichloromethane
- dry with materialThe dichloromethane was dried (MgSO4)
- concentrationconcentrated
- customto give a dark residue that
- customwas used in the next step with no further purification
Sources & evidence
- ORD record
- ord-5a6ba791f2c841d68d6fb3c6d3288391
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129424B2
Reaction notes
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