Water → 4-Chloro-2-methoxy-7-[3-(trifluoromethyl)pyridin-2-yl]-1,8-naphthyridine

HRID 1724839Notes

Reaction equation

HRID 1724839 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:14]=[C:13]([Cl:15])[C:12]2[C:7](=[N:8][C:9]([C:16]3[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][CH:11]=2)[N:6]=1.O>C1COCC1>[Cl:15][C:13]1[C:12]2[C:7](=[N:8][C:9]([C:16]3[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][CH:11]=2)[N:6]=[C:5]([O:2][CH3:1])[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 57561156HCID 57561156, compound

Product 1

HCID 575611334-Chloro-2-methoxy-7-[3-(trifluoromethyl)pyridin-2-yl]-1,8-naphthyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add sodium methoxide (4M, 1.0 mL, 4.0 mmol) to a solution of 2,4-dichloro-7-(3-trifluoromethyl-pyridin-2-yl)-[1,8]naphthyridine (1.2 g, 3.5 mmol) in THF (30 mL). Stir at room temperature overnight, add water (25 mL) and extract with ethyl acetate. Wash the combined organic extracts with brine, dry (MgSO4) and evaporate. Purify the residue by flash chromatography (elute with 1:2 hexane:ether) to give the title compound.

Workup

  1. extractionextract with ethyl acetate
  2. washWash the combined organic extracts with brine
  3. dry with materialdry (MgSO4)
  4. customevaporate
  5. customPurify the residue
  6. washby flash chromatography (elute with 1:2 hexane:ether)

Sources & evidence

ORD record
ord-f0298f102e34473aa8974a33b18c193a
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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