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

HRID 930448노트

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HRID 930448 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
75 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2896fb6781b245b4bb051602b8489293
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296734B2

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