4-Fluorobenzyl chloride → 8-(4-Fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 544449

Reaktionsgleichung

Reaktionsgleichung von HRID 544449
[OH:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CN(C)C=O>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:1][C:2]2[C:3]3[N:4]([CH:8]=[C:9]([CH3:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 8209532-Methylimidazo[1,2-a]pyridin-8-ol

Produkt 1

HCID 139002738-(4-Fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension under nitrogen of 15.0 g 8-hydroxy-2-methyl-imidazo[1,2-a]pyridine (from Step A) in 150 ml dimethylformamide maintained at 0°-5° C., was added 5.15 g 50% sodium hydride-oil dispersion in portions over 10 minutes. The mixturewas stirred in the cold 1/2 hr. and a brown solution resulted. 15.3 g 4-Fluorobenzyl chloride was added, and the solution was heated on a steam bath for 1/2 hr. The solution was poured into an ice bath and after 1/2 hour it became a brown solution. The solution was poured into 1.5 liters ice/water with vigorous stirring and the precipitate was separated by suction filtration, washed, and dried to give 8-(4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (m.p. 137° C.).

Aufarbeitung

  1. customand a brown solution resulted
  2. temperaturethe solution was heated on a steam bath for 1/2 hr
  3. additionThe solution was poured into an ice bath and after 1/2 hour it
  4. stirringwith vigorous stirring
  5. customthe precipitate was separated by suction filtration
  6. washwashed
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b8241bf63ac44730aa644686e539350d
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04450164

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