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

HRID 80832노트

반응식

HRID 80832 반응식
[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

참가 물질

5

반응물 4

HCID 6344Dichloromethane2회HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 178424916HCID 178424916, 화합물

생성물 1

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

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-57205eddb6134223b537e15bd08efcfa
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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