Pyridine → HCID 60206954, compound

HRID 1985099Notes

Reaction equation

HRID 1985099 reaction equation
O[C:2]1[C:3]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)C(N)=O.[F:15][C:16]([F:29])([F:28])[S:17]([O:20]S(C(F)(F)F)(=O)=O)(=[O:19])=[O:18].[N:30]1C=CC=C[CH:31]=1>C(OCC)(=O)C>[F:15][C:16]([F:29])([F:28])[S:17]([O:20][C:9]1[CH:10]=[CH:2][C:3]([CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:4][C:8]=1[C:31]#[N:30])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 68541012HCID 68541012, compound

Product 1

HCID 60206954HCID 60206954, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At 0° C., to a stirred solution of the hydroxy-isobutylbenzamide (3.72 g, 19.3 mmol) in pyridine (15 mL) under argon was added trifluoromethanesulfonic anhydride (10.2 ml, 57.8 mmol). The reaction mixture was eventually warmed up to room temperature and stirred overnight. The reaction was diluted with ethyl acetate, and washed with 1N HCl (×2), water (×1) and brine (×1), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography (5% ethyl acetate: hexane) to afford 2.66 g of the desired product as a clear oil (50% yield). 1H NMR (CDCl3) δ 7.56 (s, 1 H), 7.50 (d, J=8 Hz, 1 H), 7.43 (d, J=8 Hz, 1 H), 2.57 (d, J=8 Hz, 2 H), 1.92 (m, 1 H), 0.97 (d, J=4 Hz, 6 H).

Workup

  1. washwashed with 1N HCl (×2), water (×1) and brine (×1)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash column chromatography (5% ethyl acetate: hexane)

Sources & evidence

ORD record
ord-969c309ba95b4c0abac5c338c2ce0eee
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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