Lithium Hydroxide → HCID 67974579, compound

HRID 706582Notes

Reaction equation

HRID 706582 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][N:11]3[C:19]4[CH:18]=[CH:17][C:16]([F:20])=[C:15]([C:21]([O:23]C)=[O:22])[C:14]=4[C:13]([CH3:25])=[N:12]3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Li+]>C1COCC1.Cl>[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][N:11]3[C:19]4[CH:18]=[CH:17][C:16]([F:20])=[C:15]([C:21]([OH:23])=[O:22])[C:14]=4[C:13]([CH3:25])=[N:12]3)[CH:7]=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67976266HCID 67976266, compound

Product 1

HCID 67974579HCID 67974579, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-((6-cyclopropylpyridin-2-yl)methyl)-5-fluoro-3-methyl-1H-indazole-4-carboxylate (0.310 g, 0.913 mmol) was subjected to 1M aqueous lithium hydroxide (1.83 mL, 1.83 mmol) in 10 mL of THF for 16 hours at reflux. The mixture was then diluted with 1M aqueous HCl (to pH 4), and extracted twice with EtOAc. The combined organic extracts were dried over sodium sulfate and concentrated to give 0.206 g (69%) of the title compound.

Workup

  1. temperatureat reflux
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-424c2400b0604e1da86baa57f7dd578d
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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