Tributylvinyltin → 6-Ethenyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1271704노트

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HRID 1271704 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>CN(C=O)C.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>[CH:13]([C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)=[CH2:14]

참가 물질

5

반응물 2

HCID 81998TributylvinyltinHCID 110963256-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one

생성물 1

HCID 184545136-Ethenyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one수율 60%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
105 °C

실험 절차

6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one (113e) (4.6 g, 20.3 mmole) and tributyl(vinyl)tin (7.7 g, 24.4 mmole) were dissolved in DMF (200 mL) and the solution was degassed with nitrogen. (Ph3P)4Pd (590 mg, 0.5 mmole) was added to the solution. The reaction was heated to 105° C. under nitrogen overnight, then was cooled to room temperature and filtered through a sintered glass funnel. The filtrate was washed with NH4OH and extracted with EtOAc (2×150 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound (2.1 g, 60%) as an off white solid: MS (ES) m/e 175 (M+H)+.

후처리

  1. customthe solution was degassed with nitrogen
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered through a sintered glass funnel
  4. washThe filtrate was washed with NH4OH
  5. extractionextracted with EtOAc (2×150 mL)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c0d8523c87354d54ba36574e0cccb338
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205408B2

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