Potassium tert-butoxide → 5-Chloro-2-(3-(trifluoromethyl)pyridin-2-yl)-[1,8]naphthyridine

HRID 1724879Notes

Reaction equation

HRID 1724879 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]([C:20]([F:23])([F:22])[F:21])=[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]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:17]=[CH:16][N:15]=1)=[N:1]2

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 462035412-Amino-4-chloropyridine-3-carbaldehydeHCID 534031371-[3-(Trifluoromethyl)pyridin-2-yl]ethan-1-one

Product 1

HCID 462035425-Chloro-2-(3-(trifluoromethyl)pyridin-2-yl)-[1,8]naphthyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Dissolve 2-amino-4-chloronicotinaldehyde (78 mg, 0.5 mmol) and 2-acetyl-3-trifluoromethylpyridine (95 mg, 0.5 mmol) in anhydrous THF (2.0 mL) and cool it to −20° C. under N2 atmosphere. Add in portion t-BuOK (112 mg, 1.0 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 saturated aq. ammonium chloride (10 mL), filter the solid, wash the solid with water and dry under high vacuum to afford desired product as a cream colored solid.

Workup

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

Sources & evidence

ORD record
ord-0518b5abde744cca9da77fc08432951e
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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