Pyridine → HCID 86592854, compound

HRID 351235Notes

Reaction equation

HRID 351235 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][O:17][C:18]1[N:23]=[CH:22][C:21]([N:24]2[C:28]([C:29]3[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=3)=[CH:27][C:26]([O:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[N:25]2)=[CH:20][CH:19]=1.N1C=CC=CC=1>C(Cl)Cl>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:32]1[CH:31]=[CH:30][C:29]([C:28]2[N:24]([C:21]3[CH:22]=[N:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[N:25]=[C:26]([O:36][CH2:37][C:38]([F:40])([F:39])[F:41])[CH:27]=2)=[CH:34][CH:33]=1)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 135737368HCID 135737368, compound

Product 1

HCID 86592854HCID 86592854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trifluoromethanesulfonic anhydride (207 μl) in CH2Cl2 (1 mg) was added to a solution of 4-[1-(6-methoxy-3-pyridinyl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazol-5-yl]phenol (300 mg) and pyridine (199 μl) in CH2C12 (3 ml) under ice-bath cooling. The mixture was stirred at same temperature for 1 hour. The reaction was quenched by adding saturated aqueous ammonium chloride solution (5 ml) The mixture was partitioned between AcOEt and 1M HCl. The mixture was washed with saturated aqueous sodiumbicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give 4-[l-(6-methoxy-3-pyridinyl)-3-(2,2,2-trifluoro-ethoxy)-1H-pyrazol-5-yl]phenyl trifluoromethane-sulfonate (439 mg) as an oil.

Workup

  1. temperaturecooling
  2. customThe reaction was quenched
  3. additionby adding saturated aqueous ammonium chloride solution (5 ml) The mixture
  4. customwas partitioned between AcOEt and 1M HCl
  5. washThe mixture was washed with saturated aqueous sodiumbicarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92d038341a0946639c5019bdf361afcf
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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