Hydrochloric Acid → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoic acid

HRID 563404Notes

Reaction equation

HRID 563404 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:17]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:18][C:19]([O:21]C)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67005620methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoate

Product 1

HCID 670058063-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoate (700 mg, 1.87 mmol) was dissolved in 45 mL MeOH/H2O (8:1) and treated with NaOH (2 M, 10.8 mmol, 5.4 mL). The reaction was complete in 2 hours and was acidified with 1 M HCl and extracted 3×EtOAc, the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give pure 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoic acid (620 mg, 92%) as a clear oil. MS found: (M+H)+=361

Workup

  1. extractionextracted 3×EtOAc
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-417dda5154ab4f1bad212ec5b794897c
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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