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

HRID 1510609Notes

Reaction equation

HRID 1510609 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-26b9eedceb744fe9af2dbf107bb956b6
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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