Trifluoroacetic acid → 6-fluoro-1-(piperidin-4-yl)-1H-indazole

HRID 512863Notes

Reaction equation

HRID 512863 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89614504tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 539239646-fluoro-1-(piperidin-4-yl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate prepared as in STEP 1 above (998 mg, 3.10 mmol) in DCM (20 mL) at 0° C. was added TFA (10 mL). The resulting mixture was then stirred for 1 hour. The solvent was removed in vacuo. To the resulting residue was added 0.5N NaOH (15 mL), followed repeated extraction with CHCl3. The organic layer was dried with MgSO4 and filtered to yield 6-fluoro-1-(piperidin-4-yl)-1H-indazole.

Workup

  1. customThe solvent was removed in vacuo
  2. additionTo the resulting residue was added 0.5N NaOH (15 mL)
  3. extractionextraction with CHCl3
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-05a761273e034f1fb71ef13db4eae075
Source dataset
uspto-grants-2015_08
Patent number
US09102669B2

Reaction notes

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