Potassium Carbonate → 5-Fluoro-1-(2-fluorophenyl)-3-{[(3S)-piperidin-3-yl]methoxy}-1H-indazole

HRID 30416Notes

Reaction equation

HRID 30416 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[N:7]=[C:6]2[O:19][CH2:20][C@H:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.O>[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[N:7]=[C:6]2[O:19][CH2:20][C@H:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68531262HCID 68531262, compound

Product 1

HCID 532498785-Fluoro-1-(2-fluorophenyl)-3-{[(3S)-piperidin-3-yl]methoxy}-1H-indazoleYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-5-Fluoro-1-(2-fluoro-phenyl)-3-(piperidin-3-ylmethoxy)-1H-indazole hydrochloride (14.0 g, 37 mmol) was suspended in ethyl acetate (100 ml) and a 1 M solution of K2CO3 in water (100 ml) was added. The resulting mixture was vigorously stirred, which caused the solid to dissolve completely. After 1 hour, the two layers were separated and the aqueous layer was extracted twice with 50 ml of ethyl acetate. The combined organic extracts were washed with brine and dried over MgSO4. The solvent was removed under vacuum to give 11.9 g (94%) of the free base (S)-5-fluoro-1-(2-fluoro-phenyl)-3-(piperidin-3-ylmethoxy)-1H-indazole as a very thick yellow oil. 1H and 19F NMR spectra agreed with the structure.

Workup

  1. dissolutionto dissolve completely
  2. customthe two layers were separated
  3. extractionthe aqueous layer was extracted twice with 50 ml of ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e432df09004c4084a65e770c804a3a0b
Source dataset
uspto-grants-2008_09
Patent number
US07423054B2

Reaction notes

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