Sodium hydride → HCID 59149664, compound

HRID 2069313Notes

Reaction equation

HRID 2069313 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH2:9]([O:11][C:12](=[O:28])[CH:13]=[CH:14][C:15]1[CH:16]=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)[CH3:10]>CS(C)=O>[CH2:9]([O:11][C:12]([C@@H:13]1[CH2:2][C@H:14]1[C:15]1[CH:16]=[N:17][C:18]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)=[O:28])[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 68706213HCID 68706213, compound

Product 1

HCID 59149664HCID 59149664, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

100 ml of dry dimethyl sulfoxide were added slowly to a mixture of 9.30 g (42.3 mmol) of trimethylsulfoxonium iodide and 976 mg (40.1 mmol) of sodium hydride. The mixture was stirred at room temperature for 15 min, and then 8.5 g (31.3 mmol) of 3-[6-(4-fluoro-phenyl)-pyridin-3-yl]-acrylic acid ethyl ester were added. The reaction mixture was stirred at room temperature for 18 h and then poured onto ice/water and extracted with ethyl acetate. The combined organic phases were dried and evaporated. The obtained raw product was purified by column chromatography (silica gel, dichloromethane). Yield: 6.75 g.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. additionpoured onto ice/water
  3. extractionextracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customevaporated
  6. customThe obtained raw product
  7. customwas purified by column chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-40c1d052082e4e0f8969fbff48c64ed1
Source dataset
uspto-grants-2012_10
Patent number
US08299102B2

Reaction notes

Loading…