Anisole → Ethyl (5-chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetate

HRID 1372791Notes

Reaction equation

HRID 1372791 reaction equation
C1(OC)C=CC=CC=1.[Cl:9][C:10]1[C:11]([NH:23][C:24]([C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28](CC3C=CC(OC)=CC=3)[N:27]=2)=[O:25])=[CH:12][C:13]([F:22])=[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=1>FC(F)(F)C(O)=O>[Cl:9][C:10]1[C:11]([NH:23][C:24]([C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][N:27]=2)=[O:25])=[CH:12][C:13]([F:22])=[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 44607520HCID 44607520, compound

Product 1

HCID 44606313Ethyl (5-chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of anisole (288 μl, 2.66 mmol), trifluoroacetic acid (10 ml), and ethyl (5-chloro-2-fluoro-4-(1-(4-methoxybenzyl)-3-indazolylcarbonylamino)phenyl)acetate (880 mg, 1.77 mmol) was heated under reflux for 15 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. Water (50 ml) was added to the residue. The crystals thus precipitated were collected by filtration under reduced pressure and washed with water. The crude crystals thus obtained were recrystallized from chloroform-methanol, whereby ethyl (5-chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetate (531 mg, 80%) was obtained as a colorless crystalline powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. temperatureAfter cooling
  4. distillationthe reaction mixture was distilled under reduced pressure
  5. customto remove the solvent
  6. additionWater (50 ml) was added to the residue
  7. customThe crystals thus precipitated
  8. filtrationwere collected by filtration under reduced pressure
  9. washwashed with water
  10. customThe crude crystals thus obtained
  11. customwere recrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-5f3270e639cc4b26889c8b0a1a0a63d7
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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