Sodium Chloride → HCID 59278682, compound
Reaction equation
C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([NH2:40])[CH:31]=[CH:32][C:33]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1.Cl[C:42]1[N:47]=[C:46]([O:48][CH3:49])[N:45]=[C:44]([O:50][CH3:51])[N:43]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:51][O:50][C:44]1[N:45]=[C:46]([O:48][CH3:49])[N:47]=[C:42]([NH:40][C:30]2[CH:31]=[CH:32][C:33]([N:34]3[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]3)=[C:28]([O:27][CH3:26])[CH:29]=2)[N:43]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
Palladium acetate (5.0 mg, 0.022 mmol) and (2-biphenylyl) dicyclohexylphosphine (16 mg, 0.046 mmol) were dissolved under an atmosphere of argon in dioxane (2 mL) and stirred for 10 min at 20° C. This solution was added at 20° C. under an atmosphere of nitrogen to a flask containing 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (116 mg, 0.57 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (100 mg, 0.57 mmol) and potassium carbonate (1.57 g, 11.4 mmol) in 3 ml of dioxane. The resulting mixture was refluxed over night under argon, poured into a saturated aqueous solution of sodium chloride and extracted 3 times with ethyl acetate. The organic layer was dried, evaporated and the residue purified by column chromatography on silica gel using dichloromethane/methanol (98:2 v/v) as eluent to yield the title compound (18 mg, 9%) as a yellowish solid.
Workup
- additionThis solution was added at 20° C. under an atmosphere of nitrogen to a flask
- temperatureThe resulting mixture was refluxed over night under argon
- extractionextracted 3 times with ethyl acetate
- customThe organic layer was dried
- customevaporated
- customthe residue purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-71dd8d4fe6ea4f1abdf8185f60472fab
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389717B2
Reaction notes
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