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

HRID 385490

反応式

HRID 385490 の反応式
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

参加物

6

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
147.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2f3bbce24b54a4fa176006bd43234d3
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

関連ノート

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