Dimethyl Sulfoxide → HCID 68034693, compound

HRID 2409462Notes

Reaction equation

HRID 2409462 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:16][C:15]=1[CH:26]([C:28]1[N:29]([S:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)(=[O:43])=[O:42])[C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[C:32]([C:37]([F:40])([F:39])[F:38])[CH:31]=2)[OH:27])([O-:13])=[O:12].C(N(CC)CC)C>ClCCl>[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:16][C:15]=1[C:26]([C:28]1[N:29]([S:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)(=[O:42])=[O:43])[C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[C:32]([C:37]([F:39])([F:40])[F:38])[CH:31]=2)=[O:27])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66588230HCID 66588230, compound

Product 1

HCID 68034693HCID 68034693, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-80 °C

Procedure

Into a 50 mL 3-neck round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of dimethlysulfoxide (156 mg, 2.00 mmol, 3.73 equiv) in dichloromethane (5 mL). This was followed by the addition of oxalyl dichloride (127 mg, 1.00 mmol, 1.87 equiv) dropwise with stirring at −80° C. The resulting solution was stirred for 10 min at −80° C. in a liquid nitrogen bath. To this was added a solution of (2-nitro-5-(piperidin-1-yl)phenyl)(1-(phenylsulfonyl)-6-(trifluoromethyl)-1H-indol-2-yl)methanol (300 mg, 0.54 mmol, 1.00 equiv) in dichloromethane (5 mL) dropwise with stirring at −80° C. The resulting solution was stirred for an additional 60 min at −80° C. To the mixture was added triethylamine (400 mg, 3.96 mmol, 7.39 equiv) dropwise with stirring at −80° C. The resulting solution allowed to warm to −20° C. over 60 minutes. The solution was diluted with 50 mL of DCM. The mixture was washed with 1×30 mL of water and 1×30 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 300 mg of intermediate if as orange oil.

Workup

  1. customInto a 50 mL 3-neck round bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 10 min at −80° C. in a liquid nitrogen bath
  4. stirringwith stirring at −80° C
  5. stirringThe resulting solution was stirred for an additional 60 min at −80° C
  6. stirringwith stirring at −80° C
  7. temperatureto warm to −20° C. over 60 minutes
  8. washThe mixture was washed with 1×30 mL of water and 1×30 mL of brine
  9. dry with materialThe mixture was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-020e11452618425184009c8f8b201dc0
Source dataset
uspto-grants-2014_08
Patent number
US08815908B2

Reaction notes

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