Sodium hydride → HCID 59739576, compound

HRID 1192941Notes

Reaction equation

HRID 1192941 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[C:17]([S:19]([C:22]1[CH2:26][C:25]([CH3:28])([CH3:27])[O:24][N:23]=1)(=[O:21])=[O:20])=[CH2:18]>CS(C)=O>[F:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[C:11]=1[C:17]1([S:19]([C:22]2[CH2:26][C:25]([CH3:28])([CH3:27])[O:24][N:23]=2)(=[O:20])=[O:21])[CH2:2][CH2:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 59739544HCID 59739544, compound

Product 1

HCID 59739576HCID 59739576, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (0.28 g, 1.25 mmol) was added to a suspension of sodium hydride (60% by weight in paraffin oil) (0.052 g, 1.3 mmol) in DMSO (4 ml). The mixture was stirred for 30 minutes at room temperature. A solution of 3-[1-(2,6-difluoro-phenyl)-ethenesulfonyl]-5,5-dimethyl-4,5-dihydroisoxazole (prepared according to Example P12) (80% purity) (0.3 g, 0.8 mmol) in DMSO (2 ml) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction was quenched by addition of saturated aqueous ammonium chloride solution and the mixture was extracted several times with diethyl ether. The combined organic phases were dried over magnesium sulfate and concentrated. Purification by chromatography on silica gel (eluent: ethyl acetate/hexane) gave the product (Compound No. 1.01 in Table 27) (70 mg, 28% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. customThe reaction was quenched by addition of saturated aqueous ammonium chloride solution
  3. extractionthe mixture was extracted several times with diethyl ether
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (eluent: ethyl acetate/hexane)
  7. customgave the product (Compound No. 1.01 in Table 27) (70 mg, 28% yield)

Sources & evidence

ORD record
ord-c25222dddada410792c372f8b504abe6
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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