Picolinic acid → N-(3-fluoro-4-(3-methyl-3-butenoyl)phenyl)pyridine-2-carboxamide

HRID 13425

Reaction equation

HRID 13425 reaction equation
[CH3:1][C:2](=[CH2:6])[CH2:3][Mg]Cl.O1CCCC1.[F:12][C:13]1[CH:14]=[C:15]([NH:25][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[O:27])[CH:16]=[CH:17][C:18]=1[C:19](N(OC)C)=[O:20].N1C=CC=CC=1C(O)=O>O>[F:12][C:13]1[CH:14]=[C:15]([NH:25][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[O:27])[CH:16]=[CH:17][C:18]=1[C:19](=[O:20])[CH2:3][C:2]([CH3:6])=[CH2:1]

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 8028TetrahydrofuranHCID 23145523N-(3-fluoro-4-((methoxy(methyl)amino)carbonyl)phenyl)pyridine-2-carboxamideHCID 178448200HCID 178448200, compound

Product 1

HCID 23145243N-(3-fluoro-4-(3-methyl-3-butenoyl)phenyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.89 ml of (2-methyl-2-propen-1-yl)magnesium chloride (0.50 M tetrahydrofuran solution) was added to a tetrahydrofuran (10 ml) solution of 500 mg of N-(3-fluoro-4-((methoxy(methyl)amino)carbonyl)phenyl)pyridine-2-carboxamide obtained in the same method as in Example 145 (step 3) or in accordance with the method or by combining it with an ordinary method but using pyridine-2-carboxylic acid, with cooling with ice. The reaction liquid was stirred for 3 hours with cooling with ice, and then water was poured into the reaction solution, extracted with ethyl acetate and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1) to obtain the entitled compound.

Workup

  1. customobtained in the same method as in Example 145 (step 3) or in accordance with the method
  2. temperaturewith cooling with ice
  3. customThe reaction liquid
  4. temperaturewith cooling with ice
  5. extractionextracted with ethyl acetate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1)
  9. customto obtain the entitled compound

Sources & evidence

ORD record
ord-9581c41b61054aff8661bb529241a2ff
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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