Cesium carbonate → HCID 67777888, compound

HRID 1026355Notes

Reaction equation

HRID 1026355 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])=[CH:18][N:17]=1)([OH:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[CH3:11][O:10][CH2:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[CH2:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])=[CH:18][N:17]=3)([CH3:14])[O:15][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 67777663HCID 67777663, compound

Product 1

HCID 67777888HCID 67777888, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(2-bromo-4-(methoxymethoxy)phenyl)-2-(5-(triisopropylsilyloxy)pyridin-2-yl)propan-2-ol (9.6 g), copper iodide(I) (3.5 g), cesium carbonate (5.1 g) in toluene (60 mL, containing ca. 0.6 mL DMF) was heated to reflux overnight. The mixture was filtrated and the solid was washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to afford the title compound (8 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtrated
  4. washthe solid was washed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-d5c5e5f887c6433eb65142abdc481f10
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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