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

HRID 1183048

Reaktionsgleichung

Reaktionsgleichung von HRID 1183048
[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 (XXII) (1 eq) was dissolved in DCM and cooled to 0° C. before adding pyridine (2.2 eq) and isobutyryl chloride (XXIII) (1.1 eq). The reaction mixture was stirred at room temperature 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 (XXIV) as an 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-5f765fd3d4b744f195bc7604e7579a39
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664241B2

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