Perfluoro-1-butanesulfonyl fluoride → HCID 58110138, compound

HRID 1803223Notes

Reaction equation

HRID 1803223 reaction equation
[C:1]1([C:7]2[N:12]3[N:13]=[C:14]([OH:16])[CH:15]=[C:11]3[CH2:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[F:27][C:28]([F:43])([S:39](F)(=[O:41])=[O:40])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32]>C1COCC1.CCOC(C)=O>[F:43][C:28]([F:27])([S:39]([O:16][C:14]1[CH:15]=[C:11]2[CH2:10][CH2:9][CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:12]2[N:13]=1)(=[O:41])=[O:40])[C:29]([F:37])([F:38])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32]

Participants

6

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178515405HCID 178515405, compound

Product 1

HCID 58110138HCID 58110138, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step AAH (7): To a soln of 7-phenyl-4,5-dihydropyrazolo[1,5-a]pyridin-2-ol (500 mg, 2.356 mmol) in THF (15 mL) was added NaHMDS (1.0 M in THF, 2.94 mL, 2.94 mmol) at −78° C. under nitrogen. After stirring for 10 min, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1281 mg, 4.24 mmol) was added. The mixture was allowed to warm from −78° C. to rt over 3 h. The reaction was diluted with EtOAc (200 mL) and washed sequentially with 0.1 N aqueous sodium hydroxide, water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (30% EtOAc/hexanes) to afford 7-phenyl-4,5-dihydropyrazolo[1,5-a]pyridin-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (1.0 g, 86% yield). LC-MS (M+H)+ 495.12.

Workup

  1. temperatureto warm from −78° C. to rt over 3 h
  2. washwashed sequentially with 0.1 N aqueous sodium hydroxide, water, and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-b8b3a67e0ab34b18b4d9f92cee09bf42
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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