Acetic Acid → HCID 136339637, compound
Reaction equation
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].S([O-])([O-])(=O)=O.[Mg+2].[OH:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23]2[N:28]=[N:27][C:26]([O:29][CH3:30])=[C:25]([C:31](=O)[CH3:32])[CH:24]=2)=[CH:18][C:17]=1[CH3:34].C(O)(=O)C>CC(N(C)C)=O>[NH:4]1[C:3]2[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:32]=[C:31]1[C:25]1[CH:24]=[C:23]([C:19]2[CH:20]=[C:21]([CH3:22])[C:16]([OH:15])=[C:17]([CH3:34])[CH:18]=2)[N:28]=[N:27][C:26]=1[O:29][CH3:30]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
205 mg of 2-bromoaniline and 72 mg of anhydrous magnesium sulfate are suspended in 7 ml dimethylacetamide. 325 mg of 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-ethanone and 86.6 μl acetic acid are added and the reaction is degassed with argon. 330 mg of tripotassium phosphate and 61 mg of bis(tri-tert-butylphosphine) palladium (0) are added and the reaction is degassed with argon. The reaction is heated to 140° C. for 5 h. The solution is poured into water and extracted with ethyl acetate. The solvent is removed under reduced pressure. The product is purified by silica gel chromatography, eluting with a gradient of ethyl acetate in heptane. Yield 105 mg. LC-MS (ES+) 346 (M+H)+.
Workup
- customthe reaction is degassed with argon
- addition330 mg of tripotassium phosphate and 61 mg of bis(tri-tert-butylphosphine) palladium (0) are added
- customthe reaction is degassed with argon
- additionThe solution is poured into water
- extractionextracted with ethyl acetate
- customThe solvent is removed under reduced pressure
- customThe product is purified by silica gel chromatography
- washeluting with a gradient of ethyl acetate in heptane
Sources & evidence
- ORD record
- ord-6779c452773b45de9e0bbf133906ec75
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968546B2
Reaction notes
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