Dimethyl Sulfoxide → HCID 59455071, compound

HRID 1401436Notes

Reaction equation

HRID 1401436 reaction equation
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[F:12][C:13]([F:23])([F:22])[C:14]1[N:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][CH:15]=1>C1COCC1>[F:23][C:13]([F:22])([F:12])[C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[CH2:8][O:21]2)=[CH:18][N:19]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehyde

Product 1

HCID 59455071HCID 59455071, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

DMSO is added to NaH (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents stirred for 10 min. after which the solution of 6-(trifluoromethyl)pyridine-3-carbaldehyde (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h; the reaction is monitored by LCMS. After completion, the reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get the crude product.

Workup

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture is cooled to 0° C
  3. additionis added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

Sources & evidence

ORD record
ord-2c49eca2729c40f5a9c3fa97e4f36119
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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