Reaction equation
CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:19]1([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[N:28]2[CH2:32][CH2:31][NH:30][C:29]2=[O:33])[CH2:21][CH2:20]1.[Cl:34][C:35]1[CH:40]=[C:39](I)[CH:38]=[CH:37][N:36]=1>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[Cl:34][C:35]1[CH:40]=[C:39]([N:30]2[CH2:31][CH2:32][N:28]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][C:22]=3[CH:19]3[CH2:21][CH2:20]3)[C:29]2=[O:33])[CH:38]=[CH:37][N:36]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 120 °C
Procedure
Copper iodide (6.5 mg, 0.034 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (4.8 mg, 0.034 mmol) and potassium phosphate (219.3 mg, 1.034 mmol) were added to a solution of 1,4-dioxane (5 mL) previously purged with nitrogen (10 minutes). The reaction mixture was purged with argon for 10 minutes, followed by the addition of 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 70 mg, 0.344 mmol) and 2-chloro-4-iodopyridine (99.09 mg, 0.413 mmol). The reaction mixture was heated to reflux at 120° C. overnight. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was concentrated to yield the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 42 mg of the product (41% yield).
Workup
- custompreviously purged with nitrogen (10 minutes)
- customThe reaction mixture was purged with argon for 10 minutes
- temperatureThe reaction mixture was heated
- temperatureThe reaction mixture was cooled
- custompartitioned between ethyl acetate and water
- concentrationThe organic layer was concentrated
- customto yield the crude product
- customPurification by column chromatography on silica gel (2% methanol in CHCl3)
Sources & evidence
- ORD record
- ord-f5e55f224cc042d09e56ecfca1061a20
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09339501B2
Linked notes
Loading…