Ammonium Chloride → HCID 46830909, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][C:13](=[O:15])[CH:12]=[CH:11][NH:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].C([Li])CCC.[Br:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:23]=1[CH2:32][C:33](Cl)=[O:34].[Cl-].[NH4+]>C1COCC1>[Br:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:23]=1[CH2:32][C:33]([N:10]1[CH:11]=[CH:12][C:13](=[O:15])[CH2:14][CH:9]1[C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])=[O:34]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -75 °C
Procedure
To 75 mg of 2-(3-cyanophenyl)-2,3-dihydro-pyridin-4-one in 8 ml THF at −75° C. was added 0.2 ml 2.5M n-butyl lithium. The mixture is stirred under argon at −75° C. for 10 minutes and then 106 mg 2-(2-bromo-4,5-dimethoxy-phenyl)acetyl chloride in 2 ml THF was added slowly. The reaction mixture was then stirred at −75° C. for 30 minutes, then allowed to warm to room temperature and was stirred for an additional 30 minutes. To this mixture was added 10 ml saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography of the residue gave 45 mg 3-{1-[2-(2-bromo-4,5-dimethoxy-phenyl)-acetyl]-4-oxo-1,2,3,4-tetrahydro-pyridin-2-yl}-benzonitrile. MS (M+H) 457.
Workup
- stirringThe reaction mixture was then stirred at −75° C. for 30 minutes
- temperatureto warm to room temperature
- stirringwas stirred for an additional 30 minutes
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-60d7add99bd84232827589f9964a9339
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153808B2
Reaction notes
Loading…