Methanol → HCID 67387130, compound

HRID 444930Notes

Reaction equation

HRID 444930 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[C:9]([C:20]([OH:22])=[O:21])=[N:10][C:11]([O:18][CH3:19])=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.OS(O)(=O)=O.[CH3:28]O>>[CH3:7][C:4]1[N:3]([C:8]2[C:9]([C:20]([O:22][CH3:28])=[O:21])=[N:10][C:11]([O:18][CH3:19])=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 584423133-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid2×

Product 1

HCID 67387130HCID 67387130, compound

Procedure

3-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (Intermediate D2)(500 mg, 1.591 mmol) in methanol (15.91 ml) was treated with H2SO4 (0.0424 ml, 0.795 mmol) and the solution was heated at reflux for overnight. The solvent removed was removed in vacuo and the resulting brown oil was neutralised to pH 7 using saturated sodium bicarbonate. The mixture was extracted with EtOAc (20 ml) and the combined organic extracts were washed with water (20 ml), brine (20 ml), passed though a phase separator and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with iso-hexane: EtOAc (gradient of 0 to 10% EtOAc) afforded the title compound as an off-white powder.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for overnight
  3. customThe solvent removed
  4. customwas removed in vacuo
  5. extractionThe mixture was extracted with EtOAc (20 ml)
  6. washthe combined organic extracts were washed with water (20 ml), brine (20 ml)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with iso-hexane

Sources & evidence

ORD record
ord-563a5af2f22e470a86065a1a90e94667
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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