Citric Acid → HCID 67044507, compound

HRID 2367103Notes

Reaction equation

HRID 2367103 reaction equation
CC([Si](C(C)C)(C(C)C)[N:5]1[C:13]2[C:8](=[CH:9][C:10](C(C3C=CC=CC=3C#N)=O)=[CH:11][CH:12]=2)[CH:7]=[N:6]1)C.[C:30](O)(=O)[CH2:31][C:32]([CH2:37][C:38]([OH:40])=[O:39])([C:34]([OH:36])=O)O.[CH2:43](O)[CH3:44]>[OH-].[Na+].C(OCC)(=O)C>[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([C:34]([C:32]3[CH:31]=[CH:30][CH:44]=[CH:43][C:37]=3[C:38]([OH:40])=[O:39])=[O:36])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 702EthanolHCID 67044556HCID 67044556, compound

Product 1

HCID 67044507HCID 67044507, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-({1-[tris(1-methylethyl)silyl]-1H-indazol-5-yl}carbonyl)benzonitrile in ethanol (2.0 mL) and 20% aqueous sodium hydroxide solution (2.0 mL) was refluxed for 30 min. Solid citric acid was added to pH 3-4. The reaction mixture was diluted with ethyl acetate, dried (sodium sulfate), filtered and concentrated in vacuo to give 0.19 g (>100% crude yield) of 2-(1H-indazol-5-ylcarbonyl)benzoic acid. NMR analysis confirmed the concurrent loss of the triisopropylsilyl protecting group during this step. The crude acid was used without further purification for the next step. 1H NMR (400 MHz, d4-MeOH): 8.14 (m, 1H), 8.10 (m, 1H), 8.05 (m, 1H), 7.75 (m, 3H), 7.63 (d, 1H), 7.57 (m, 1H).

Workup

  1. dry with materialdried (sodium sulfate)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9622fc5af352482293f53dda89d3982d
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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