Ethyl Acrylate → 7-Methoxy-1,5-naphthyridin-2(1H)-one

HRID 385486Notes

Reaction equation

HRID 385486 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][N:3]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(N(CC)CC)C>[NH2:8][C:7]1[C:2](/[CH:13]=[CH:12]/[C:11]([O:15][CH2:16][CH3:17])=[O:14])=[N:3][CH:4]=[C:5]([O:9][CH3:10])[CH:6]=1.[CH3:10][O:9][C:5]1[CH:6]=[C:7]2[C:2]([CH:13]=[CH:12][C:11](=[O:14])[NH:8]2)=[N:3][CH:4]=1

Participants

6

Reactant 2

HCID 8821Ethyl AcrylateHCID 202004202-Chloro-5-methoxypyridin-3-amine

Product 2

HCID 578154107-Methoxy-1,5-naphthyridin-2(1H)-oneHCID 68105232ethyl (2E)-3-(3-amino-5-methoxypyridin-2-yl)acrylate

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
155 °C

Procedure

To 1.0 g of 2-chloro-5-methoxypyridin-3-amine, 0.82 mL of ethyl acrylate, 4.2 mL of triethylamine, and 0.16 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 150 to 160° C. for 6 hours in a sealed tube. The reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=100:0 to 90:10 to obtain 0.41 g of ethyl (2E)-3-(3-amino-5-methoxypyridin-2-yl)acrylate and 0.25 g of 7-methoxy-1,5-naphthyridin-2(1H)-one as light brown solids.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resultant residue was purified by flash silica gel column chromatography
  4. washelution with chloroform

Sources & evidence

ORD record
ord-a086e5911642442f8b2a38298447f647
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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