Sodium Hydroxide → HCID 21687336, compound

HRID 1464574Notes

Reaction equation

HRID 1464574 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([F:29])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:7][CH:6]=1.[OH-].[Na+]>C1COCC1.C(O)(C)C>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[C:21]([F:29])[C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19086731HCID 19086731, compound

Product 1

HCID 21687336HCID 21687336, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[6-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)indazol-1-yl]propionate prepared as described in Example 2 (30 mgs) was dissolved in THF (0.1 cm3) and isopropanol (0.28 cm3). 1.73M sodium hydroxide (0.04 cm3) was added and the mixture stirred at room temperature for 8 hours and left to stand overnight. The solvent was removed under vacuum and the residue dissolved in water (2 cm3). 2M hydrocloric acid (0.035 cm3) was added dropwise with stirring. After 1.5 hours the solid product was filtered off, washed with water and air dried to give 2-[6-(2-chloro-6-fluoro-4-trifluoromethylphenoxy) indazol-1-yl]propionic acid (11 mgs) as a white solid. Compound No 4 was prepared by an analogous process using appropriate reactants.

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue dissolved in water (2 cm3)
  5. addition2M hydrocloric acid (0.035 cm3) was added dropwise
  6. stirringwith stirring
  7. filtrationAfter 1.5 hours the solid product was filtered off
  8. washwashed with water and air
  9. customdried

Sources & evidence

ORD record
ord-b1ba2095d40944de9e2e7db3d2197695
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

Loading…