Ethanol → 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid

HRID 1037524Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2C(C#N)=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:28]([C:27]([OH:25])=[O:29])=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred suspension of compound (vi) (3.3 g, 8.6 mmol) in ethanol (35 mL) was added aqueous NaOH (3.44 g, 86 mmol) and the reaction mixture was heated to 90° C. and maintained for 15 h when TLC and LCMS showed the absence of SM and formation of product. Concentration of the solvent gave a crude residue which was dissolved in water and filtered. The filtrate was acidified with dilute HCl at which time the product precipitated and was filtered to give the crude product which was purified by acid-base treatment to give 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid (vii) (2.2 g, 63%).

Workup

temperaturemaintained for 15 h when TLC and LCMS
customConcentration of the solvent gave a crude residue which
filtrationfiltered
customprecipitated
filtrationwas filtered
customto give the crude product which
customwas purified by acid-base treatment

Sources & evidence

ORD record: ord-8cba4bb1f3c0476b89a3b81eac0682fa
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546389B2

Reaction notes

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