Tetrabutylammonium Fluoride → HCID 23114784, compound

HRID 2080498Notes

Reaction equation

HRID 2080498 reaction equation
[Cl:1][C:2]1[C:3]([CH:17]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:18]2[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:19]=2[F:26])=[CH:4][C:5]([N:8](S(C)(=O)=O)[S:9]([CH3:12])(=[O:11])=[O:10])=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[C:3]([CH:17]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)(=[O:28])=[O:29])[C:18]2[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:19]=2[F:26])=[CH:4][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23114643HCID 23114643, compound

Product 1

HCID 23114784HCID 23114784, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After N-[5-chloro-4-[(4-chlorophenylsulfonyl)(5-cyano-2-fluorophenyl)methyl]pyridin-2-yl]-N-(methylsulfonyl)methanesulfonamide (80 mg, 0.11 mmol) was dissolved in tetrahydrofuran (3 ml), a tetrahydrofuran solution (1.0M, 0.15 ml, 0.15 mmol) of tetrabutylammonium fluoride was added to the resulting solution at 0° C. The resulting mixture was stirred at room temperature for 1 hour. The residue obtained by concentrating the reaction mixture under reduced pressure was subjected to silica gel chromatography. The fraction obtained from the n-hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure to afford a white solid. The resulting white solid was washed with ether to give the title compound (32 mg, 0.06 mmol, 46%) as a white powder.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. customThe fraction obtained from the n-hexane
  4. concentrationethyl acetate=2:1 eluate was concentrated under reduced pressure
  5. customto afford a white solid
  6. washThe resulting white solid was washed with ether

Sources & evidence

ORD record
ord-7bbd798d95774a0eb4ef71627d2eedf6
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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