Pyridine → N-(5-bromopyridin-3-yl)-2-methylpropanamide

HRID 889134

Reaktionsgleichung

Reaktionsgleichung von HRID 889134
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:19])[CH:16]([CH3:18])[CH3:17]>C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH:3]=[N:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 8176813-Amino-5-bromopyridine

Produkt 1

HCID 68195778N-(5-bromopyridin-3-yl)-2-methylpropanamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Amino-5-bromo pyridine (XVIII) (1 eq) was dissolved in DCM and cooled to 0° C. before adding pyridine (2.2 eq) and isobutyryl chloride (XIX) (1.1 eq). The reaction mixture was stirred at r.t. for 15 h until TLC showed the reaction was complete. The reaction mixture was diluted with DCM and washed with water. The organic extract was dried, concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford N-(5-bromopyridin-3-yl)isobutyramide (XX) as a off white solid, (71% yield). 1H NMR (CDCl3) δ ppm 8.55-8.35 (m, 3H), 7.32 (s, 1H), 2.59-2.48 (m, 1H), 1.28-1.27 (d, 6H); ESIMS found C9H11BrN2O m/z 243.05 (M+H).

Aufarbeitung

  1. washwashed with water
  2. extractionThe organic extract
  3. customwas dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5cba7cac7c3140dcb823249f3b217b29
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252812B2

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