Sodium hydride → 1-phenyl-1,8-naphthyridin-4(1H)-one

HRID 1063537노트

반응식

HRID 1063537 반응식
[NH:1](/[C:8](/NC(C)C)=[CH:9]\[C:10]([C:12]1[C:13](Cl)=[N:14][C:15](Cl)=[C:16](F)[CH:17]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C=O)C.O>[C:2]1([N:1]2[C:13]3[C:12](=[CH:17][CH:16]=[CH:15][N:14]=3)[C:10](=[O:11])[CH:9]=[CH:8]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 24758Sodium hydrideHCID 60061202(2Z)-3-anilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-3-(isopropylamino)-2-propen-1-one

생성물 1

HCID 222789461-phenyl-1,8-naphthyridin-4(1H)-one수율 86.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

(2Z)-3-Anilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-3-(isopropylamino)-2-propen-1-one (40.0 mg, 0.109 mmol) was dissolved in 4 mL of DMF. NaH (8.70 mg, 0.217 mmol, 60% dispersion in oil) was added and the reaction was heated to 85° C. under argon for 2 h. The reaction mixture was cooled to room temperature and diluted with water and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue using Biotage silica gel chromatography eluting with 100% EtOAc to 95:5 EtOAc:MeOH provided 7-chloro-6-fluoro-2-isopropylamino)-1-phenyl-1,8-naphthyridin-4(1H)-one (21 mg, 64%) as a white solid: LCMS RT: 2.57 min, MH+: 332.2.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue
  7. washeluting with 100% EtOAc to 95:5 EtOAc

출처 및 근거

ORD 기록
ord-2742a6b035694b5ea1c5bbdc9ef1228d
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06964971B2

반응 노트

불러오는 중…