Trifluoroacetic acid → HCID 58042357, compound

HRID 2048050Notes

Reaction equation

HRID 2048050 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([O:22][C:23]2[C:35]([F:36])=[CH:34][C:26]([C:27]([O:29]C(C)(C)C)=[O:28])=[C:25]([F:37])[CH:24]=2)[CH:12]=[N:13][C:14]=1[O:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C(Cl)Cl.O>[Cl:8][C:9]1[CH:10]=[C:11]([O:22][C:23]2[C:35]([F:36])=[CH:34][C:26]([C:27]([OH:29])=[O:28])=[C:25]([F:37])[CH:24]=2)[CH:12]=[N:13][C:14]=1[O:15][CH:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58042498HCID 58042498, compound

Product 1

HCID 58042357HCID 58042357, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl 4-{[5-chloro-6-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-yl]oxy}-2,5-difluorobenzoate (Preparation 23, 0.28 g, 0.64 mmol) in DCM (10 mL) and stirred at room temperature for 16 hours. The reaction mixture was diluted with water (50 mL), and extracted with DCM (3×50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to yield a yellow oil, which was purified by silica gel chromatography eluting with EtOAc to afford an off white solid. The solid was triturated with 4:1, heptane: EtOAc to afford the title compound as a white solid (0.24 g):

Workup

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield a yellow oil, which
  6. customwas purified by silica gel chromatography
  7. washeluting with EtOAc
  8. customto afford an off white solid
  9. customThe solid was triturated with 4:1, heptane

Sources & evidence

ORD record
ord-5f09f7cd147f408ebe4f8fa28c638b75
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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