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

HRID 1063537ノート

反応式

HRID 1063537 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-2742a6b035694b5ea1c5bbdc9ef1228d
出典データセット
uspto-grants-2005_11
特許番号
US06964971B2

反応ノート

読み込み中…