Cesium carbonate → Methyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-6-methylpyridine-4-carboxylate

HRID 43762

Reaction equation

HRID 43762 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.Cl[C:22]1[CH:27]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[CH:25]=[C:24]([CH3:32])[N:23]=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:27]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[CH:25]=[C:24]([CH3:32])[N:23]=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]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2759833Methyl 2-Chloro-6-methylisonicotinateHCID 86648698Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate hydrochloride

Product 1

HCID 86648710Methyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-6-methylpyridine-4-carboxylateYield 7.4%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The same operation as in Example (42a) was performed using benzyl cis(±)-[3-methoxypiperidin-4-yl]carbamate hydrochloride obtained in Example (160a) (384 mg, 1.45 mmol), methyl 2-chloro-6-methylpyridine-4-carboxylate (243 mg, 1.31 mmol), palladium acetate (32.7 mg, 0.15 mmol), BINAP (181 mg, 0.29 mmol) and cesium carbonate (1.42 g, 4.36 mmol), to obtain 40.1 mg of the title compound as a yellow oily substance (6.7%).

Sources & evidence

ORD record
ord-07df82e89cf24c2d836442d94e64ad27
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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