Pyridine → HCID 18680108, compound

HRID 2299003Notes

Reaction equation

HRID 2299003 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3]O.N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH:28]([CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([CH:41]3[CH2:43][CH:42]3[C:44]3[CH:45]=[C:46]4[C:51](=[CH:52][CH:53]=3)[CH:50]=[C:49]([C:54]#[N:55])[CH:48]=[CH:47]4)[CH:39]=2)[CH2:34][CH2:33][NH:32]1)([CH3:30])[CH3:29].C([O-])([O-])=O.[K+].[K+]>ClCCl.CN(C=O)C.O>[CH:28]([CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([CH:41]3[CH2:43][CH:42]3[C:44]3[CH:45]=[C:46]4[C:51](=[CH:52][CH:53]=3)[CH:50]=[C:49]([C:54]#[N:55])[CH:48]=[CH:47]4)[CH:39]=2)[CH2:34][CH2:33][N:32]1[CH2:3][C:2]([F:6])([F:5])[F:1])([CH3:30])[CH3:29]

Participants

9

Reactant 5

HCID 1049PyridineHCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 67749Trifluoromethanesulfonic anhydrideHCID 18680150HCID 18680150, compound

Product 1

HCID 18680108HCID 18680108, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2,2-trifluoroethanol (0.88 mL, 12 mmol) and pyridine (0.9 mL, 12 mmol)in dichloromethane (10 mL) at 0° C. was treated dropwise with trifluoromethanesulfonic anhydride (2.0 mL, 12 mmol), stirred for 15 minutes, warmed to room temperature, and stirred for 18 hours. The solution (0.7 mL, 0.84 mmol) was added dropwise to a mixture of Example 20A (150 mg, 0.41 mmol) and K2CO3 (172 mg, 1.2 mmol) in DMF (1.1 mL), stirred for 24 hours, treated with water, and extracted with dichloromethane. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel using 10% ethyl acetate/hexanes to provide the desired product.

Workup

  1. stirringstirred for 18 hours
  2. stirringstirred for 24 hours
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel using 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a1100cff58d24a2fbb8d0daa49fb4c6c
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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