Thionyl Chloride → 2-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

HRID 586372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586372
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:15]=1[CH2:16][CH2:17][CH3:18]>C(Cl)Cl.CCOC(C)=O>[Cl:3][CH2:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:15]=1[CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 223350472-Hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

Produkt 1

HCID 223350602-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Thionyl chloride (125 mg, 1.06 mmol) is added to a solution of 2-hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine (100 mg, 0.53 mmol) in CH2Cl2 (3 mL) at 0° C. under nitrogen with magnetic stirring. After 1 hour, the reaction is diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The solution is then dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure to obtain 2-chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine as a colorless oil. TLC (10% MeOH/CH2Cl2) Rf=0.60. Step 5. Preparation of 3-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe solution is then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8ad0518c2cf24898b0c7b4a219712732
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936617B2

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