Sodium Hydroxide → HCID 117859510, compound

HRID 1486236Notes

Reaction equation

HRID 1486236 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:20])[C:14]([C:15]([O:17]CC)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:21])[CH:7]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:20])[C:14]([C:15]([OH:17])=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:21])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117859492HCID 117859492, compound

Product 1

HCID 117859510HCID 117859510, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 0.440 g (1.22 mmol, 1 eq.) of ethyl 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate from Example 3A in 12.7 ml of dioxane was admixed with 4.9 ml (4.88 mmol, 4.0 eq.) of 1 N aqueous sodium hydroxide solution and the mixture was stirred at 90° C. for 36 h. Subsequently, the reaction mixture was concentrated and the precipitated solids were filtered off. The filtrate was acidified with 6 N aqueous hydrochloric acid and stirred briefly, and the precipitated solids were filtered off, washed with water and dried. 248 mg of the title compound were obtained (61% of theory, 60% purity), which was converted further without further purification.

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated
  2. filtrationthe precipitated solids were filtered off
  3. stirringstirred briefly
  4. filtrationthe precipitated solids were filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-beb3280fff04421b91a3bb75cb97f83d
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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