Acetic Acid → HCID 70031142, compound

HRID 397534Notes

Reaction equation

HRID 397534 reaction equation
[NH2:1][C:2]1[C:3]([F:14])=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([F:8])=[CH:6][CH:7]=1.CC(O)=O.[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[CH2:20]>CO>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:19][CH2:20][NH:1][C:2]1[C:3]([F:14])=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([F:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75212-VinylpyridineHCID 10965547Methyl 2-(3-amino-2,6-difluorophenyl)acetate

Product 1

HCID 70031142HCID 70031142, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 402 mg (2.0 mmol) of methyl 3-amino-2,6-difluorophenylacetate (prepared in step 3 of example 24) in 15 mL of MeOH was treated with 1.1 mL (20.0 mmol) of HOAc and 0.28 mL (2.6 mmol) of 2-vinylpyridine. The reaction mixture was stirred at reflux for 16 h. The mixture was cooled and the acetic acid was removed in vacuo. The residue was dissolved in EtOAc and washed with saturated NaHCO3 (4×5 mL), water (1×10 mL) and brine. Column chromatography (1:4 EtOAc/Hex) afforded methyl 3-(2-pyridylethyl)amino-2,6-difluorophenylacetate.

Workup

  1. temperatureat reflux for 16 h
  2. temperatureThe mixture was cooled
  3. customthe acetic acid was removed in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated NaHCO3 (4×5 mL), water (1×10 mL) and brine

Sources & evidence

ORD record
ord-d57aae8940ad42a39594f288979475f2
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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