N-Fluorobenzenesulfonimide → HCID 59739620, compound

HRID 1192948Notes

Reaction equation

HRID 1192948 reaction equation
[Cl:1][CH:2]([C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[F:20])[S:3]([C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1)(=[O:5])=[O:4].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:31])(=O)=O)=CC=1>C1COCC1>[Cl:1][C:2]([C:13]1[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=1[F:19])([F:31])[S:3]([C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 588007N-FluorobenzenesulfonimideHCID 59739546HCID 59739546, compound

Product 1

HCID 59739620HCID 59739620, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phosphazene base 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda5-5,4-lambda5-5-catenadi(phosphazene) (P2-tBu) (2M in THF) (0.38 ml, 0.77 mmol) was added dropwise to a solution of 3-[chloro-(2,6-difluoro-phenyl)-methanesulfonyl]-5,5-dimethyl-4,5-dihydroisoxazole (0.2 g, 0.64 mmol) in THF (2 ml), and the solution was stirred for 10 minutes at room temperature. N-Fluorobenzenesulfonimide (NFSI) (0.15 g, 0.77 mmol) was added and the mixture was stirred for 1 hour. The reaction was quenched by addition of aqueous hydrochloric acid (2M). The mixture was diluted with ethyl acetate and the two phases were separated. The organic phase was washed several times with brine, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (Compound No. 1.21 of Table 27) as a white solid (44 mg, 98% yield).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customThe reaction was quenched by addition of aqueous hydrochloric acid (2M)
  3. additionThe mixture was diluted with ethyl acetate
  4. customthe two phases were separated
  5. washThe organic phase was washed several times with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-738319fc9d264ccabd4fafd244a84aef
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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