Dichloromethane → 4-chloro-2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 80832ノート

反応式

HRID 80832 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:18]=[C:17](O)[C:16]2[C:15](=[O:20])[N:14]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:13][CH2:12][C:11]=2[N:10]=1.C(=O)(O)[O-].[Na+].[OH-].[Na+].C(Cl)[Cl:39]>>[Cl:39][C:17]1[C:16]2[C:15](=[O:20])[N:14]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:28])[CH3:29])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH:18]=1

参加物

5

反応物 4

HCID 6344Dichloromethane2 回HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 178424916HCID 178424916、化合物

生成物 1

HCID 712406884-chloro-2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

実験手順

To a solution of crude 2-(2,6-dimethylphenyl)-4-hydroxy-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (1.4 g, 3.50 mmol) in DCM (35.0 mL) was added Vilsmeier's reagent (0.895 g, 6.99 mmol) as a solid in one portion and the reaction mixture stirred at room temperature. After 2 h 500 mg of Vilsmeier's reagent was added and stirring continued. After 35 min an additional portion of 200 mg of Vilsmeier's reagent was added and stirring continued. After 15 min the reaction mixture was diluted with DCM and poured into saturated aqueous sodium bicarbonate solution containing 1 N NaOH. The layers were separated and the aqueous layer was extracted with DCM (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by FCC (0-20% EtOAc/heptane) to provide 4-chloro-2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one. MS (ESI+) m/z 419.2 (M+H)+.

後処理

  1. stirringstirring
  2. stirringstirring
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (2×)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by FCC (0-20% EtOAc/heptane)

出典と根拠

ORDレコード
ord-57205eddb6134223b537e15bd08efcfa
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

反応ノート

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