Water → 1-isopropyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxylic acid

HRID 85446Notes

Reaction equation

[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[CH:9]=[C:8]([C:18]([O:20]C)=[O:19])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2].O.O[Li].O>C1COCC1>[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[CH:9]=[C:8]([C:18]([OH:20])=[O:19])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of methyl 1-isopropyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxylate (750 mg, 2.64 mmol) in THF:H2O (30 mL) was added LiOH.H2O (330 mg, 7.85 mmol) and the resulting mixture was refluxed at 80° C. for 8 h. THF was distilled off under reduced pressure and the aqueous layer was acidified with 10% HCl (to pH ˜5) at 0° C. The precipitated solid was collected by filtration and dried to afford the title compound I-isopropyl-6-(1H-pyrazol-4-yl)-1H-indazole-4-carboxylic acid as an off-white solid (540 mg, 76%). LCMS (ES+) m/z=271.09.

Workup

distillationTHF was distilled off under reduced pressure
customwas acidified with 10% HCl (to pH ˜5) at 0° C
filtrationThe precipitated solid was collected by filtration
customdried

Sources & evidence

ORD record: ord-2007fba41ec34858b54f206b0f87a139
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846935B2

Reaction notes

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