Cesium carbonate → HCID 86613824, compound

HRID 2075654Notes

Reaction equation

HRID 2075654 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([Br:12])[C:9]2[C:4](=[CH:5][C:6]([CH2:13]Br)=[CH:7][CH:8]=2)[N:3]=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][CH2:13][C:6]3[CH:5]=[C:4]4[C:9]([C:10]([Br:12])=[CH:11][C:2]([Br:1])=[N:3]4)=[CH:8][CH:7]=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 86613820HCID 86613820, compound

Product 1

HCID 86613824HCID 86613824, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

2,4-Dibromo-7-bromomethyl-quinoline (1.0 g, 2.6 mmol), 4-(3-fluoro-5-hydroxy-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (1a, 670 mg, 2.6 mmol), and cesium carbonate (1.7 g, 5.3 mmol) were suspended in DMF (15 mL) and stirred overnight at room temperature. The mixture was diluted with EtOAc and saturated aqueous NH4Cl, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography to give the desired product, 1b.

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

Sources & evidence

ORD record
ord-42e371f52e8545f7b5a5a93c9db61557
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

Loading…