Pyridine → HCID 89656290, compound

HRID 930947Notes

Reaction equation

HRID 930947 reaction equation
[Br:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:9][C:5]([C:6]([NH2:8])=O)=[C:4]([NH:20][S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])[CH:3]=1.O1CCOCC1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[Br:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:9][C:5]([C:6]#[N:8])=[C:4]([NH:20][S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])[CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 89655984HCID 89655984, compound

Product 1

HCID 89656290HCID 89656290, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of Example 324e (230 mg, 0.53 mmol) and dioxane (1.5 mL) was added pyridine (0.14 mL, 1.7 mmol) followed by 2,2,2-trifluoroacetic anhydride (0.14 mL, 0.99 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 5-40% ethyl acetate/heptane gradient) to afford the title compound (135 mg, 61% yield).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, 5-40% ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-d83c233ed6b8438d84ab4e22ac1812c5
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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