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

HRID 1425413Notes

Reaction equation

HRID 1425413 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O:13][C@H:14]1[C@@H:19]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:18][CH2:17][NH:16][CH2:15]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>[CH2:23]([O:22][C:21]([NH:20][C@H:19]1[CH2:18][CH2:17][N:16]([C:2]2[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH3:11])[CH:3]=2)[CH2:15][C@H:14]1[O:13][CH3:12])=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 53438912Methyl 5-bromo-3-methylthiophene-2-carboxylateHCID 86648490Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate

Product 1

HCID 86648826Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-methylthiophene-2-carboxylateYield 23.6%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The same operation as in Example (244b) was performed using methyl 5-bromo-3-methylthiophene-2-carboxylate obtained in Example (245a) (218 mg, 0.93 mmol), benzyl cis(±)-(3-methoxypiperidin-4-yl)-carbamate obtained in Example (40b) (270 mg, 1.02 mmol), palladium acetate (42 mg, 0.19 mmol), BINAP (115 mg, 0.19 mmol) and cesium carbonate (423 mg, 1.30 mmol), to obtain 92 mg of the title compound as a yellow oily substance (24%).

Sources & evidence

ORD record
ord-5822d4e8043040dd8b09d10fa61a8889
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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