Reaction equation
C[Al](C)C.[CH3:5][NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:15]([C:17]1[C:22]2[N:23]=[C:24]([C:26]([O:28]CC)=O)[O:25][C:21]=2[C:20]([F:31])=[C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:18]=1[CH3:38])#[N:16].Cl>ClCCl>[C:15]([C:17]1[C:22]2[N:23]=[C:24]([C:26]([N:6]([CH3:5])[CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:28])[O:25][C:21]=2[C:20]([F:31])=[C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:18]=1[CH3:38])#[N:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 1.80 ml, 1.85 mmol) was dropwise added at room temperature to a dichloromethane (3 ml) solution of N-methylphenethylamine (269 μl, 1.85 mmol), and stirred for 25 minutes. Subsequently, a dichloromethane (3 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (300 mg, 925 μl) was dropwise added and stirred for 14.5 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform.
Workup
- stirringstirred for 14.5 hours
- additionwas added to the reaction liquid
- temperaturewith cooling with ice
- stirringby stirring at room temperature
- customthe reaction liquid
- extractionwas extracted with chloroform
Sources & evidence
- ORD record
- ord-3c23cc3f34664b59a15fc35c79f1eae3
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737166B2
Linked notes
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