N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide → HCID 86716070, compound

HRID 627486Notes

Reaction equation

HRID 627486 reaction equation
CON(C)[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][CH:6]=1.[Cl:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][CH:23]=1>C1COCC1>[Cl:17][C:18]1[CH:23]=[C:22]([C:4]([C:5]2[CH:6]=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:10]=2)=[O:15])[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 23116945N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide2×HCID 178478127HCID 178478127, compound

Product 1

HCID 86716070HCID 86716070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (1.23 g, 5.25 mmol, Intermediate 15, step b) in THF (12 mL) at 4° C. was added 0.5 M (3-chlorophenyl)magnesium bromide in THF (12.7 mL, 6.35 mmol). The mixture was stirred at 4° C. to room temperature overnight, and quenched with NH4Cl (aqueous). The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic phases were dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography (40 g silica gel column, 0-70% EtOAc in heptanes) to give the title compound as an oil, which solidified upon standing.

Workup

  1. customquenched with NH4Cl (aqueous)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (40 g silica gel column, 0-70% EtOAc in heptanes)

Sources & evidence

ORD record
ord-15c642f432974fbc94f6c25f9409480d
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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