Cesium carbonate → HCID 86648860, compound

HRID 1425448Notes

Reaction equation

HRID 1425448 reaction equation
[CH2:1]([N:8]([C@H:19]1[CH2:24][CH2:23][NH:22][CH2:21][C@H:20]1[O:25][CH3:26])[C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:28]1[CH:29]=[C:30]([CH:35]=[C:36]([F:38])[CH:37]=1)C(OC)=O.[C:39](=[O:42])([O-])[O-:40].[Cs+].[Cs+].O1CCOC[CH2:46]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH2:1]([N:8]([C:9]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:18])[C@H:19]1[CH2:24][CH2:23][N:22]([C:35]2[C:36]([F:38])=[C:37]([CH:28]=[CH:29][CH:30]=2)[C:39]([O:40][CH3:46])=[O:42])[CH2:21][C@H:20]1[O:25][CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 21942598Methyl 3-bromo-5-fluorobenzoateHCID 86712358Benzyl benzyl[cis(+/-)-3-methoxypiperidin-4-yl]carbamate

Product 1

HCID 86648860HCID 86648860, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The same operation as in Example (42a) was performed using benzyl benzyl[cis(±)-3-methoxypiperidin-4-yl]carbamate obtained in Example (259c) (507 mg, 1.4 mmol), methyl 3-bromo-5-fluorobenzoate known in the literature (Org. Lett., 9(23), 2007, 4893-4896) (400 mg, 1.7 mmol), tris(dibenzylideneacetone)dipalladium (65 mg, 0.07 mmol), (±)-BINAP (178 mg, 0.29 mmol), cesium carbonate (1.02 g, 3.2 mmol), 1,4-dioxane (10 mL) and DMF (2.5 mL), to obtain 31 mg of the title compound as a yellow oily substance (4%).

Sources & evidence

ORD record
ord-e1eb9a195c694e089485638d72b7337f
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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