O-Xylene → 8-Ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

HRID 656905노트

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HRID 656905 반응식
[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13]CC=C)[CH:9]=[CH:8]2)[CH3:2].[C:18]1(C)[C:19](C)=CC=C[CH:23]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:19][CH:18]=[CH2:23])[C:10](=[O:13])[CH:9]=[CH:8]2)[CH3:2]

참가 물질

4

반응물 2

HCID 7237O-XyleneHCID 689954698-Ethyl-7-fluoro-2-(2-propen-1-yloxy)-1,5-naphthyridine

생성물 1

HCID 689929808-Ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one수율 27%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
150 °C

실험 절차

8-Ethyl-7-fluoro-2-(2-propen-1-yloxy)-1,5-naphthyridine (0.660 g, 2.84 mmol) was dissolved in xylene (14 ml) at rt under argon, whereupon tetrakis(triphenylphosphine)palladium (0.329 g, 0.284 mmol) was added. The reaction was then heated to 150° C. for 30 mins. Reaction was then cooled, a solid then precipitated out which was filtered. The filtrate was then purified by column chromatography on silica gel eluting with 0-100% EtOAc in hexane then 0-20% MeOH in EtOAc gradient to give title compound as a white solid (0.181 g, 27%).

후처리

  1. additionwas added
  2. customReaction
  3. temperaturewas then cooled
  4. customa solid then precipitated out which
  5. filtrationwas filtered
  6. customThe filtrate was then purified by column chromatography on silica gel eluting with 0-100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-4b91c623732b4dd6bbe63d67594f45de
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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