Cesium carbonate → HCID 86613829, compound

HRID 2075683Notes

Reaction equation

HRID 2075683 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:14])=[CH:8][C:9]([Cl:13])=[N:10]2)=[CH:5][CH:4]=1.[CH3:15][O:16][C:17]([C:19]1([C:25]2[CH:30]=[C:29]([OH:31])[CH:28]=[C:27]([F:32])[CH:26]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.[NH4+].[Cl-]>[CH3:15][O:16][C:17]([C:19]1([C:25]2[CH:26]=[C:27]([F:32])[CH:28]=[C:29]([O:31][CH2:2][C:3]3[CH:12]=[C:11]4[C:6]([C:7]([Cl:14])=[CH:8][C:9]([Cl:13])=[N:10]4)=[CH:5][CH:4]=3)[CH:30]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 67091086HCID 67091086, compoundHCID 86613818HCID 86613818, compound

Product 1

HCID 86613829HCID 86613829, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

7-Bromomethyl-2,4-dichloro-quinoline (1.4 g, 4.8 mmol), 4-(3-Fluoro-5-hydroxy-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (5a, 1.2 g, 4.8 mmol), and cesium carbonate (3.1 g, 9.6 mmol) were suspended in DMF (20 mL) and stirred overnight at room temperature. The mixture was diluted with EtOAc and saturated NH4Cl, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 5b.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-33d2e0ee45f94eda97d401b0a704e2cf
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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