Cesium carbonate → Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyridine-3-carboxylate

HRID 1425241Notes

Reaction equation

HRID 1425241 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:23]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([CH3:28])=[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:29]([O:31][CH3:32])=[O:30])[C:25]([CH3:28])=[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]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 10867045Methyl 5-chloro-2-methylnicotinateHCID 86648698Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate hydrochloride

Product 1

HCID 86648719Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyridine-3-carboxylateYield 86.4%

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) (190 mg, 0.63 mmol), methyl 5-chloro-2-methylpyridine-3-carboxylate (117 mg, 0.63 mmol), palladium acetate (14.2 mg, 0.06 mmol), BINAP (78.6 mg, 0.13 mmol) and cesium carbonate (617 mg, 1.89 mmol), to obtain 225 mg of the title compound as a brown oily substance (86%).

Sources & evidence

ORD record
ord-d0e05fe3aafa48c7a2e5cf021b7813e3
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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