Phosphorus oxychloride → 3,8-Dichloro-5-fluoro-1,7-naphthyridine

HRID 1526555ノート

反応式

HRID 1526555 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=O)[NH:7][CH:8](OC)[CH:9]([F:12])[C:10]=2[CH:11]=1.P(Cl)(Cl)([Cl:18])=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([F:12])[CH:8]=[N:7][C:6]=2[Cl:18]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 867157463-chloro-5-fluoro-6-methoxy-6,7-dihydro-1,7-naphthyridin-8(5H)-one

生成物 1

HCID 867157453,8-Dichloro-5-fluoro-1,7-naphthyridine収率 79.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
75 °C

実験手順

A vial was charged with 3-chloro-5-fluoro-6-methoxy-6,7-dihydro-1,7-naphthyridin-8(5H)-one (7.5 g, 32.5 mmol), acetonitrile (130 mL) and phosphorus oxychloride (9.09 mL, 98 mmol), and the mixture was stirred at 75° C. for 15 hours. The mixture was concentrated, and the crude material was purified by silica gel chromatography, eluting with 0-50% ethyl acetate in heptanes, to provide the title compound (5.57 g, 25.7 mmol, 79% yield) as a white solid. LC/MS (ESI+) m/z=217(M+H)+.

後処理

  1. concentrationThe mixture was concentrated
  2. customthe crude material was purified by silica gel chromatography
  3. washeluting with 0-50% ethyl acetate in heptanes

出典と根拠

ORDレコード
ord-aa5fff7a763f4b40bd4a25a9a16621a7
出典データセット
uspto-grants-2015_07
特許番号
US09085576B2

反応ノート

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