Lithium hydroxide, monohydrate → 1-isopropyl-3-methyl-6-(pyridin-3-yl)-1H-indazole-4-carboxylic acid

HRID 1476460Notes

Reaction equation

HRID 1476460 reaction equation
[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:9]=[C:8]([C:19]([O:21]C)=[O:20])[C:7]=2[C:6]([CH3:23])=[N:5]1)([CH3:3])[CH3:2].C(N1C2C=C(C3C=C4C=CNC4=NC=3)C=C(C(OC)=O)C=2C=N1)(C)C.O[Li].O>C1COCC1.O>[CH:1]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:9]=[C:8]([C:19]([OH:21])=[O:20])[C:7]=2[C:6]([CH3:23])=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 67464617HCID 67464617, compoundHCID 67467136Methyl 1-isopropyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxylate

Product 1

HCID 674682551-isopropyl-3-methyl-6-(pyridin-3-yl)-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 1-isopropyl-3-methyl-6-(pyridin-3-yl)-1H-indazole-4-carboxylate, 1 (0.5 g, 1.618 mmol) in a mixture of THF and H2O (30 mL) was added LiOH.H2O (0.2 g, 4.85 mmol) and the mixture was refluxed at 80° C. for 8 h. THF was distilled off and the aqueous layer was adjusted to pH˜5 with 10% HCl at 0° C. and the precipitated solid was collected by filtration and dried to afford 1-isopropyl-3-methyl-6-(pyridin-3-yl)-1H-indazole-4-carboxylic acid as an off-white solid (0.51 g). LCMS (ES+) m/z: 296.7.

Workup

  1. distillationTHF was distilled off
  2. customwas adjusted to pH˜5 with 10% HCl at 0° C.
  3. filtrationthe precipitated solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-05d5c7bc0d844f7498fce7c903f4e977
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

Loading…