Chloroacetaldehyde → 5-Bromo-6-fluoroimidazo[1,2-a]pyridine

HRID 1922746

Reaktionsgleichung

Reaktionsgleichung von HRID 1922746
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[F:9].Cl[CH2:11][CH:12]=O>>[Br:1][C:2]1[N:7]2[CH:11]=[CH:12][N:8]=[C:6]2[CH:5]=[CH:4][C:3]=1[F:9]

Komponenten

3

Edukt 2

HCID 33ChloroacetaldehydeHCID 596058336-Bromo-5-fluoropyridin-2-amine

Produkt 1

HCID 596052135-Bromo-6-fluoroimidazo[1,2-a]pyridineAusbeute 89 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-bromo-5-fluoropyridin-2-ylamine (25 mg, 0.13 mmol) and chloroacetaldehyde (0.1 mL, 50 wt. % in water) in IMS (2 mL) was stirred at 100° C. in a sealed tube for 18 hours, then cooled to room temperature and loaded onto an Isolute® SCX-2 cartridge (5 g). The desired product was washed with MeOH then eluted with 2 M NH3 in MeOH to give 5-Bromo-6-fluoroimidazo[1,2-a]pyridine as a yellow oil (25 mg, 89%). 1H NMR (400 MHz, CHCl3-d): δ 7.84 (s, 1 H); 7.76 (m, 1 H); 7.61 (ddd, J=9.73, 4.67, 0.71 Hz, 1 H); 7.21-7.16 (m, 1 H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washThe desired product was washed with MeOH
  3. washthen eluted with 2 M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-1b758d13ac794e188fec9644e66fa4e2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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