Cesium carbonate → Ethyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-3-carboxylate
Reaction equation
Cl.[CH3:2][O:3][C@H:4]1[C@@H:9]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7][NH:6][CH2:5]1.Br[C:22]1[CH:23]=[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[N:26][CH:27]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:13]([O:12][C:11]([NH:10][C@H:9]1[CH2:8][CH2:7][N:6]([C:22]2[CH:23]=[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[N:26][CH:27]=2)[CH2:5][C@H:4]1[O:3][CH3:2])=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The same operation as in Example (160b) was performed using benzyl cis(±)-[3-methoxypiperidin-4-yl]carbamate hydrochloride obtained in Example (160a) (832 mg, 2.76 mmol), ethyl 5-bromopyridine-3-carboxylate (530 mg, 2.3 mmol), palladium acetate (51.72 mg, 0.23 mmol), BINAP (286.89 mg, 0.46 mmol), and cesium carbonate (2.25 g, 6.91 mmol), to obtain 487 mg of the title compound as a yellow oily substance.
Sources & evidence
- ORD record
- ord-17d2beb0a5124c0dbc9116438f2fbfd2
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927588B2
Reaction notes
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