Pivaloyl chloride → 6-Fluoro-2-pivaloylaminopyridine

HRID 132234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132234
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:15])([CH3:14])[C:11](Cl)=[O:12]>N1C=CC=CC=1>[F:1][C:2]1[N:7]=[C:6]([NH:8][C:11](=[O:12])[C:10]([CH3:15])([CH3:14])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 62493Pivaloyl chlorideHCID 27613996-Fluoropyridin-2-amine

Produkt 1

HCID 131542516-Fluoro-2-pivaloylaminopyridineAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6-fluoropyridin-2-amine (13.1 g, 117 mmol) was dissolved in anhydrous pyridine (100 mL), and cooled to 0° C. followed by fast dropwise addition of trimethylacetyl chloride (15.9 mL, 129 mmol) over 2 min. 5 min later, the resulting slurry was stirred over night at room temperature. Partial of the solvent was removed on rotary vacuum. The residue was partitioned between saturated ammonium chloride (200 mL) and EtOAc (200 mL). After separation, the organic layer was washed with brine (50 mL), dried over MgSO4, concentrated on rotary vacuum, and purified on flash chromatography eluting with 25˜75% EtOAc/Hexanes (1400 mL) to afford the expected product as a white solid(21.4 g, 93% yield); 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (s, 9 H), 6.63 (dd, J=8.06, 2.01 Hz, 1 H), 7.76 (q, J=8.14 Hz, 1 H), 7.85 (s, 1 H), 8.09 (dd, J=8.06, 1.76 Hz, 1 H); Mass spec. 197.15 (MH+), Calc. for C10H13FN2O196.1

Aufarbeitung

  1. customPartial of the solvent was removed on rotary vacuum
  2. customThe residue was partitioned between saturated ammonium chloride (200 mL) and EtOAc (200 mL)
  3. customAfter separation
  4. washthe organic layer was washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated on rotary vacuum
  7. custompurified on flash chromatography
  8. washeluting with 25˜75% EtOAc/Hexanes (1400 mL)

Quellen und Nachweise

ORD-Eintrag
ord-6a40b07d6de843328a0fb3f8f0133177
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384930B2

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