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

HRID 1271704ノート

反応式

HRID 1271704 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
105 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c0d8523c87354d54ba36574e0cccb338
出典データセット
uspto-grants-2007_04
特許番号
US07205408B2

反応ノート

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