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Hydrochloric Acid → 3-bromo-1-trityl-1H-indazole-5-carboxylic acid

HRID 1467318
Notes
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Reaction equation

HRID 1467318 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13]CC)=[O:12])[CH:9]=2)[N:4]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[Li+].[OH-].Cl>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67984870HCID 67984870, compound

Product 1

HCID 679965973-bromo-1-trityl-1H-indazole-5-carboxylic acidYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 3-bromo-1-trityl-1H-indazole-5-carboxylate (5.3 g, 20 mmol) in THF (80 mL), was added LiOH (30 mL, 1 N) and the reaction mixture was stirred at 50° C. for overnight. HCl (1 N) was added to adjust the pH˜4. Then ethyl acetated (100 mL) was added. The organic layer was separated and the aqueous layer was extract three times with ethyl acetate (20 mL each). The combined organic was washed with water (30 mL×3). Dry over Na2SO4 and concentrated on vacuum to give desired product as light yellow solid (4.8 g).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extract three times with ethyl acetate (20 mL each)
  4. washThe combined organic was washed with water (30 mL×3)
  5. dry with materialDry over Na2SO4
  6. concentrationconcentrated on vacuum

Sources & evidence

ORD record
ord-e2f426245ca04bb3b99a381e72ea3e00
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