Sodium Thiosulfate → HCID 117759731, compound

HRID 1049532Notes

Reaction equation

HRID 1049532 reaction equation
[F:1][CH:2]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])=[C:14]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[N:13]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[CH:8][CH:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O>[F:1][CH:2]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])=[C:14]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[N:13]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 117760097HCID 117760097, compound

Product 1

HCID 117759731HCID 117759731, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (3-(2-fluoro-2-(5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)ethyl)phenyl)methanol (126 mg) in DMSO (1.0 mL) was added a Dess-Martin reagent (188 mg) at room temperature, and the mixture was stirred for 20 min. To the reaction mixture was added aqueous sodium thiosulfate solution at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound as a brown oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b1b48bccc1b84a60979029b6bafcc775
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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