(E)-ethyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)acrylate → 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)propanoic acid

HRID 563381Notes

Reaction equation

HRID 563381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](/[CH:18]=[CH:19]/[C:20]([O:22]CC)=[O:21])=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1>CCO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86640303(E)-ethyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)acrylate

Product 1

HCID 670052123-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)propanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(c)(d) (E)-ethyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)acrylate (350 mg, 1.08 mmol) was dissolved in EtOH (30 mL) and hydrogenated over 10% Pd/C (70 mg) at 50 psi H2 for 4 h. The catalyst was filtered off and the solution was treated with 1 M NaOH (30 mL) and stirred for 16 h. The pH was adjusted to 4-5 with conc HCl. Most of the EtOH was removed in vacuo and the solution was extracted with EtOAc and dried over MgSO4, filtered, and conc. Obtained 320 mg (100%) of 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)propanoic acid.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe solution was treated with 1 M NaOH (30 mL)
  3. customMost of the EtOH was removed in vacuo
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-77889b008b734abfaf0af84e5ad87b1d
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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