1-(3-Chloropyridin-2-yl)ethanone → 5-Chloro-2-(3-chloropyridin-2-yl)-[1,8]naphthyridine

HRID 1724874Notes

Reaction equation

HRID 1724874 reaction equation
[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]([Cl: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]([Cl:20])=[CH:18][CH:17]=[CH:16][N:15]=1)=[N:1]2

Participants

5

Reactant 3

HCID 146449721-(3-Chloropyridin-2-yl)ethanoneHCID 23665647Potassium tert-butoxideHCID 462035412-Amino-4-chloropyridine-3-carbaldehyde

Product 1

HCID 575611615-Chloro-2-(3-chloropyridin-2-yl)-[1,8]naphthyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Dissolve 2-amino-4-chloronicotinaldehyde (312 mg, 2.0 mmol) and 2-acetyl-3-chloropyridine (310 mg, 2.0 mmol) in anhydrous THF (5.0 mL) and cool it to −20° C. under N2 atmosphere. Add in portion t-BuOK (448 mg, 4.0 mmol) to the reaction mixture and stir the mixture at 10° 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 solid.

Workup

  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

Sources & evidence

ORD record
ord-96e8cbfd6aa44777b0f8b9ec6aed11d6
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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