L-Methionine → HCID 22349418, compound

HRID 896027Notes

Reaction equation

HRID 896027 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C:18]4[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.N[C@H](C(O)=O)CCSC.CS(O)(=O)=O.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6137L-MethionineHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 22349465HCID 22349465, compound

Product 1

HCID 22349418HCID 22349418, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-Fluoro-phenyl)-5-(4-methoxy-phenoxy)-1H-indazole (0.3 grams, mmol), methionine (0.40 grams, mmol) and 3 mL of methanesulfonic acid was shaken for 24 hours at room temperature. The mixture was treated with a solution of 1.8 grams of sodium hydroxide in 20 mL of water with cooling in an ice bath, and the aqueous phase was extracted 3 times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo, affording 0.20 grams of 4-[1-(4-Fluoro-phenyl)-1H-indazol-5-yloxy]-phenol as a colorless solid. MS: 321.7 [M+H]+

Workup

  1. temperaturewith cooling in an ice bath
  2. extractionthe aqueous phase was extracted 3 times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73256930905b4f02868e7d73bad68eac
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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