Ethyl Acetate → HCID 90020871, compound

HRID 2200101Notes

Reaction equation

HRID 2200101 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([F:17])[C:13](F)=[N:14][CH:15]=1.CCOC(C)=O>CN(C=O)C>[Br:9][C:10]1[CH:11]=[C:12]([F:17])[C:13]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 145496545-Bromo-2,3-difluoropyridineHCID 178507942HCID 178507942, compound

Product 1

HCID 90020871HCID 90020871, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Mix 2-aminopyridin-4-ol (1.13 g, 10.3 mmol), 5-bromo-2,3-difluoro-pyridine (2 g, 10.3 mmol) in DMF (10 mL). Stir the mixture at 120° C. for 3 hrs. TLC (EtOAc:PE=1:1) shows the reaction is complete. Filter, add water (50 mL) to the filtrate, extract with EtOAc (50 mL×3). Combine the organic layers, dry over anhydrous Na2SO4. Concentrate to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:4) affords the title compound (1.35 g, 46.3%). MS: (M+1): 284.

Workup

  1. filtrationFilter
  2. additionadd water (50 mL) to the filtrate
  3. extractionextract with EtOAc (50 mL×3)
  4. dry with materialCombine the organic layers, dry over anhydrous Na2SO4
  5. concentrationConcentrate
  6. customto give the crude product
  7. customPurification by chromatography (silica gel, EtOAc:PE=1:4)

Sources & evidence

ORD record
ord-5d8b99116ed84c34aa28c01b415d65b6
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…