Water → HCID 59334503, compound

HRID 1639808Notes

Reaction equation

HRID 1639808 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[C:18]2[C:14](=[CH:15][N:16]([CH3:19])[N:17]=2)[C:13](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:12][CH:11]=1.O>CS(C)=O>[F:9][C:10]1[C:18]2[C:14](=[CH:15][N:16]([CH3:19])[N:17]=2)[C:13]([CH:20]2[CH2:4][CH:21]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720614HCID 66720614, compound

Product 1

HCID 59334503HCID 59334503, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Under nitrogen atmosphere, to a suspension of sodium hydride (290 mg, 7.25 mmol) in dimethyl sulfoxide (45 mL) was added trimethylsulfoxonium iodide (1.73 g, 7.86 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl (2E)-3-(7-fluoro-2-methyl-2H-indazol-4-yl)acrylate (1.50 g, 6.04 mmol) in dimethyl sulfoxide (15 mL) at 0° C., and the mixture was stirred at 70° C. for 27 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85-+50/50) to give the title compound (1.20 g, yield 76%).

Workup

  1. stirringthe mixture was stirred at 70° C. for 27 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85-+50/50

Sources & evidence

ORD record
ord-e12169f794774e0da6829e6d3b3b8fd9
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

Loading…