Cesium carbonate → HCID 58381245, compound

HRID 1025804Notes

Reaction equation

HRID 1025804 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:9]([O:11][CH3:12])=[O:10].[I:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)([CH3:30])[CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=1>CN(C=O)C>[I:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:9]([O:11][CH3:12])=[O:10])=[CH:35][CH:36]=2)([CH3:30])[CH:27]([CH3:28])[CH3:29])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 20540308Methyl 2-bromo-2-(pyridin-2-yl)acetateHCID 590267534-[1-(4-iodophenyl)-1,2-dimethylpropyl]Phenol

Product 1

HCID 58381245HCID 58381245, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (1.5 equiv.) followed by methyl bromo(pyridin-2-yl)acetate (5i) (1 equiv.) are added to a stirred solution of 5b (1 equiv.) in DMF at room temperature. After completion of reaction, the reaction mixture is quenched with saturated aqueous ammonium chloride, poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound 5c.

Workup

  1. customAfter completion of reaction
  2. customthe reaction mixture is quenched with saturated aqueous ammonium chloride
  3. additionpoured into saturated aqueous sodium bicarbonate
  4. extractionextracted three times with EtOAc
  5. washThe combined organic extracts are washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8db77b361ae54aa1aa0e88b559bb396c
Source dataset
uspto-grants-2014_05
Patent number
US08729104B2

Reaction notes

Loading…