Potassium tert-butoxide → 5-Chloro-2-(6-methoxy-3-trifluoromethyl-pyridin-2-yl)-[1,8]naphthyridine

HRID 545078Notes

Reaction equation

HRID 545078 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[CH3:11][O:12][C:13]1[N:18]=[C:17]([C:19](=O)[CH3:20])[C:16]([C:22]([F:25])([F:24])[F:23])=[CH:15][CH:14]=1.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:20][C:19]([C:17]1[C:16]([C:22]([F:23])([F:25])[F:24])=[CH:15][CH:14]=[C:13]([O:12][CH3:11])[N:18]=1)=[N:1]2

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 462035412-Amino-4-chloropyridine-3-carbaldehydeHCID 586457531-(6-Methoxy-3-trifluoromethyl-pyridin-2-yl)-ethanone

Product 1

HCID 586455165-Chloro-2-(6-methoxy-3-trifluoromethyl-pyridin-2-yl)-[1,8]naphthyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Dissolve 2-amino-4-chloronicotinaldehyde (156 mg, 1.0 mmol) and 1-(6-methoxy-3-trifluoromethyl-pyridin-2-yl)-ethanone (219 mg, 1.0 mmol) in anhydrous THF (5 mL) and cool to −40° C. under a N2 atmosphere. Add in portions t-BuOK (168 mg, 1.5 mmol) to the reaction mixture and stir the mixture at −10° C. for 2 hours. Concentrate the reaction mixture by rotary evaporation, collect the solid by filtration and air-dry to afford the title compound.

Workup

  1. concentrationConcentrate the reaction mixture
  2. customby rotary evaporation
  3. customcollect the solid
  4. filtrationby filtration
  5. customair-dry

Sources & evidence

ORD record
ord-831a8083ed5c40d09f4d68278d740993
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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