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

HRID 43755
Notes
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Reaction equation

HRID 43755 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]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 634876Binap, (A+-)-HCID 86648698Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate hydrochloride

Product 1

HCID 86648702Ethyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-3-carboxylateYield 51.2%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

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-f7084e78cd4e493192a1becde05d7c28
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536197B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes