HCID 118005488, compound → HCID 86716070, compound

HRID 1478508Notes

Reaction equation

HRID 1478508 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([C:13]1C=CC=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[C:5]2[OH:23].[Cl:24]C1C=C([Mg]Br)C=CC=1>C1COCC1>[Cl:24][C:2]1[CH:3]=[C:4]([C:5]([C:6]2[CH:7]=[N:8][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)=[O:23])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 118005488HCID 118005488, compound2×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 2: 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 provide 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-2a63c1629b374ac4a76f548ca87e778c
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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