Water → 7-Fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

HRID 656868ノート

反応式

HRID 656868 の反応式
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[N:4][CH:3]=1.[H-].[Na+].[CH2:15](I)[CH:16]=[CH2:17].O>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[N:9]2[CH2:17][CH:16]=[CH2:15])=[N:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 469008017-Fluoro-1,5-naphthyridin-2(1H)-one

生成物 1

HCID 585794677-Fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

7-Fluoro-1,5-naphthyridin-2(1H)-one (2.152 g, 13.122 mmol) was suspended in dry DMF (40 ml) under argon at 0° C., and the stirred suspension was treated with sodium hydride (1.155 g of a 60% w:w dispersion in oil, 2.2 eq.) added in portions. The suspension was allowed to warm to rt. After stirring for 30 mins at rt, the mixture was treated with allyl iodide (2.67 ml, 2.2 eq) and then stirred for a further 30 min before addition of water (100 ml). The mixture was then extracted with DCM (3×200 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated to give a residue which was purified by column chromatography on silica with a 0-10% methanol in DCM gradient to give the desired product as a light brown solid (1.683 g, 63%).

後処理

  1. additionw dispersion in oil, 2.2 eq.) added in portions
  2. extractionThe mixture was then extracted with DCM (3×200 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a residue which
  7. customwas purified by column chromatography on silica with a 0-10% methanol in DCM gradient

出典と根拠

ORDレコード
ord-99fd1e59768d4e9d81031f9de5e50b74
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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