Reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:2]=1.C[N:17]([CH:19]=O)C.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:27][CH:26]=1)=O>O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[CH:2]=[CH:1][C:6]([N:7]3[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:27][CH:26]=4)[N:17]=[C:19]3[CH2:23][CH:25]([CH3:30])[CH3:26])=[CH:5][CH:4]=2)=[CH:10][CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 4-amino-4′-chlorodiphenyl ether (1.2 eq., 6.2 mmol) in anhydrous DMF (10 mL) DIEA (3 eq. 16 mmol) was added, followed by slow addition of the 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone described above (5.2 mmol), according to General Procedure R2. The reaction mixture was stirred under nitrogen at rt until completion, as indicated by TLC or HPLC. The reaction mixture was then diluted with cold H2O and the product was extracted in EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography (Silica gel). Pure product obtained from 2–4% MeOH/DCM (yield ˜22%).
Workup
- extractionthe product was extracted in EtOAc
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- customEvaporation of solvent in vacuuo
Sources & evidence
- ORD record
- ord-7a7a8ff677d04747becc7991c5e5b003
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361678B2
Linked notes
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