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Hydrochloric Acid → 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid

HRID 1467313
Notes
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Reaction equation

HRID 1467313 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19]CC)=[O:18])[CH:15]=3)[N:10]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.CO.[OH-].[Na+].Cl>C(O)(C)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[N:10]([C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67984978ethyl 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylate

Product 1

HCID 679849753-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acidYield 98.6%

Reagents, catalysts & solvents 2

HCID 3776
Isopropanol
Solvent
HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

In a sealed flask was added ethyl 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylate (420 mg, 0.802 mmol), MeOH (6 ml), and sodium hydroxide (1N in water, 4 ml, 4.00 mmol). The resulting mixture was then heated for 60 min at a temperature of 80° C. with stirring. The mixture was then neutralized with HCl (2N in water), diluted with 10% isopropanol in chloroform, washed with water, dried with sodium sulfate, filtered, and concentrated to afford 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid (392 mg, 0.791 mmol) as a light yellow solid. The crude product was progressed to the next step without purification.

Workup

  1. washwashed with water
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7fe3d1c8fcca471b8d6273e8759085f1
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999957B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes