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

HRID 43946

Reaction equation

HRID 43946 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH:11]=[O:12])[CH:3]=1.[CH3:13][O:14][C@H:15]1[C@@H:20]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19][CH2:18][NH:17][CH2:16]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>[CH2:24]([O:23][C:22]([NH:21][C@H:20]1[CH2:19][CH2:18][N:17]([C:2]2[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH:11]=[O:12])[CH:3]=2)[CH2:16][C@H:15]1[O:14][CH3:13])=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 86648490Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamateHCID 86648830Methyl 5-bromo-3-formylthiophene-2-carboxylate

Product 1

HCID 86648831Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-formylthiophene-2-carboxylateYield 20.9%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The same operation as in Example (244b) was performed using methyl 5-bromo-3-formylthiophene-2-carboxylate obtained in Example (246b) (974 mg, 3.91 mmol), benzyl cis(±)-(3-methoxypiperidin-4-yl)-carbamate obtained in Example (40b) (1.10 g, 4.16 mmol), palladium acetate (176 mg, 0.78 mmol), BINAP (0.49 g, 0.78 mmol) and cesium carbonate (1.78 g, 5.47 mmol), to obtain 354 mg of the title compound as a yellow oily substance (21%).

Sources & evidence

ORD record
ord-e7105cf23d7d46ceb8474ab4940ef051
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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