L-Methionine → HCID 22349423, compound

HRID 896023Notes

Reaction equation

HRID 896023 reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:12]=[CH:11]3)=[CH:5][CH:4]=1.N[C@H](C(O)=O)CCSC.[OH-].[Na+].C(=O)(O)[O-].[Na+]>CS(O)(=O)=O.O>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([O:7][C:6]4[CH:23]=[CH:24][C:3]([OH:2])=[CH:4][CH:5]=4)=[CH:16][CH:15]=3)[CH:11]=[N:12]2)[CH:18]=1

Participants

7

Reactant 4

HCID 6137L-MethionineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 22349446HCID 22349446, compound

Product 1

HCID 22349423HCID 22349423, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 5-(4-Methoxy-phenoxy)-1-pyridin-3-yl-1H-indazole (0.11 grams, mmol) in 2 mL of methanesulfonic acid was treated with 0.2 grams of methionine. After stirring for 24 hours at room temperature, the mixture was treated with 1.2 grams of sodium hydroxide in 50 mL of water with cooling in an ice bath, neutralized with aqueous sodium bicarbonate, extracted 3 times with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo, affording 0.10 grams of 4-(1-Pyridin-3-yl-1H-indazol-5-yloxy)-phenol as a colorless syrup. MS: 304.4 [M+H]+

Workup

  1. temperaturewith cooling in an ice bath
  2. extractionextracted 3 times with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3047d40cbbee426784b5ae1f9fe56b78
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

Loading…