2,6-Lutidine → HCID 57561127, compound

HRID 1724834Notes

Reaction equation

HRID 1724834 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:13]=[C:12](O)[C:11]2[C:6](=[N:7][C:8]([C:15]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:9][CH:10]=2)[N:5]=1.O=P(Cl)(Cl)[Cl:27].N1C(C)=CC=CC=1C>C(Cl)(Cl)Cl>[Cl:27][C:12]1[C:11]2[C:6](=[N:7][C:8]([C:15]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:3][O:2][CH3:1])[CH:13]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 178494542HCID 178494542, compound

Product 1

HCID 57561127HCID 57561127, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-[1,8]napthyridin-4-ol (191 mg, 0.569 mmol) is dissolved in a solution of chloroform (15 mL), POCl3 (0.212 mL, 2.28 mmol) and 2,6-lutidine (0.256 mL, 2.28 mmol). The reaction is heated at reflux overnight. The mixture is concentrated under reduced pressure. The resulting residue is dissolved in EtOAc (50 mL) and extracted with water (50 mL), saturated NaHCO3(aq) (50 mL) and brine (50 mL). The organic extract is dried over Na2SO4 and the solvent removed under reduced pressure. The crude product is purified by column chromatography on silica gel eluting with hexanes/EtOAc (1:1) to yield the title compound as a white solid.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture is concentrated under reduced pressure
  4. dissolutionThe resulting residue is dissolved in EtOAc (50 mL)
  5. extractionextracted with water (50 mL), saturated NaHCO3(aq) (50 mL) and brine (50 mL)
  6. extractionThe organic extract
  7. dry with materialis dried over Na2SO4
  8. customthe solvent removed under reduced pressure
  9. customThe crude product is purified by column chromatography on silica gel eluting with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-e4c9cc343d79486481cd4188b239041a
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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