1-(3-Methylpyridin-2-yl)ethan-1-one → 5-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

HRID 1724876노트

반응식

HRID 1724876 반응식
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[C:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)(=O)[CH3:12].CC([O-])(C)C.[K+]>C1COCC1>[Cl:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[C:3]=1[CH:4]=[CH:12][C:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)=[N:1]2

참가 물질

5

반응물 3

HCID 130686691-(3-Methylpyridin-2-yl)ethan-1-oneHCID 23665647Potassium tert-butoxideHCID 462035412-Amino-4-chloropyridine-3-carbaldehyde

생성물 1

HCID 575610685-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

Dissolve 2-amino-4-chloronicotinaldehyde (156 mg, 1.0 mmol) and 2-acetyl-3-methylpyridine (136 mg, 1.0 mmol) in anhydrous THF (5.0 mL) and cool it to −20° C. under N2 atmosphere. Add in portion t-BuOK (224 mg, 2.0 mmol) to the reaction mixture and stir the mixture at 110° C. for 2 hours. Concentrate the reaction mixture under vacuum, dilute the residue with water (10 mL), filter the solid, wash the solid with water and dry under high vacuum to afford the title product as a yellow colored solid.

후처리

  1. concentrationConcentrate the reaction mixture under vacuum
  2. additiondilute the residue with water (10 mL)
  3. filtrationfilter the solid
  4. washwash the solid with water
  5. customdry under high vacuum

출처 및 근거

ORD 기록
ord-55a15a94dd2845c5881bd7d5b2d23bf3
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488740B2

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