Lithium Hydroxide → HCID 58042406, compound

HRID 2048076Notes

Reaction equation

HRID 2048076 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[C:25]([F:26])=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[CH:15][C:14]=2[F:27])[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[C:14]([F:27])=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:24][C:25]=2[F:26])[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86660846HCID 86660846, compound

Product 1

HCID 58042406HCID 58042406, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]-3,5-difluorobenzoate (Preparation 145, 426 mg, 1.06 mmol) and LiOH (100 mg) were added to a solution of THF:water (1:1) and heated at 50° C. for 3 hours. The reaction was then quenched with aqueous 1M HCl and extracted with EtOAc. The combined organics were dried and concentrated in vacuo to afford the title compound as a white solid (342 mg, 94% yield):

Workup

  1. customThe reaction was then quenched with aqueous 1M HCl
  2. extractionextracted with EtOAc
  3. customThe combined organics were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c7809bd292444818e2e7fe02994103f
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

Loading…