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

HRID 1510613

반응식

HRID 1510613 반응식
Br[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12]>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:12]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13])=[N:3][CH:4]=[C:5]([F:9])[CH:6]=1.[F:9][C:5]1[CH:6]=[C:7]2[C:2]([CH:12]=[CH:11][C:10](=[O:13])[NH:8]2)=[N:3][CH:4]=1

참가 물질

6

반응물 2

HCID 8821Ethyl AcrylateHCID 404273672-Bromo-5-fluoropyridin-3-amine

생성물 2

HCID 469008017-Fluoro-1,5-naphthyridin-2(1H)-oneHCID 68105283ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 8471Triethylamine용매

반응 조건

온도
147.5 °C

실험 절차

To 0.99 g of 2-bromo-5-fluoropyridin-3-amine, 0.67 mL of ethyl acrylate, 3.5 mL of triethylamine, and 0.13 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 145 to 150° C. for 5 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 0.37 g of ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate and 0.15 g of 7-fluoro-1,5-naphthyridin-2(1H)-one as light brown solids.

후처리

  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

출처 및 근거

ORD 기록
ord-5f9e88e7673d4358b8e829909d845ee2
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211908B2

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