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

HRID 1724876Notes

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]([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

Participants

Conditions

Temperature: -20 °C

Procedure

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.

Workup

concentrationConcentrate the reaction mixture under vacuum
additiondilute the residue with water (10 mL)
filtrationfilter the solid
washwash the solid with water
customdry under high vacuum

Sources & evidence

ORD record: ord-55a15a94dd2845c5881bd7d5b2d23bf3
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488740B2

Reaction notes

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