4-Nitrophenyl chloroformate → 3-[5-(2-Fluoro-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid 4-nitro-phenyl ester

HRID 2097599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097599
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C([N:27]1[CH2:30][CH:29]([O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[F:44])=[CH:34][N:33]=2)[CH2:28]1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:27]2[CH2:30][CH:29]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[F:44])=[CH:34][N:33]=3)[CH2:28]2)=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Komponenten

4

Edukt 2

HCID 821294-Nitrophenyl chloroformateHCID 580730992-(1-Benzhydryl-azetidin-3-yloxy)-5-(2-fluoro-phenyl)-pyridine

Produkt 1

HCID 580731093-[5-(2-Fluoro-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid 4-nitro-phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-nitrophenyl chloroformate (734 mg g, 3.64 mmol) was added to a stirred solution of 2-(1-Benzhydryl-azetidin-3-yloxy)-5-(2-fluoro-phenyl)-pyridine (996 mg, 2.43 mol) in dichloromethane (25 mL) at ambient temperature. The resulting solution was stirred at ambient temperature for 18 hr, diluted with dichloromethane (150 mL) and washed sequentially with sat. aqueous sodium hydrogen carbonate solution (3×150 mL) then sat. sodium chloride solution (150 mL). The organic phase was dried over magnesium sulphate and filtered. Filtrate solvents were removed in vacuo and the residue was purified by trituration with Methyl tertiary butyl ether (25 mL) to give after filtration a yellow solid (786 mg, 79%).

Aufarbeitung

  1. washwashed sequentially with sat. aqueous sodium hydrogen carbonate solution (3×150 mL)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customFiltrate solvents were removed in vacuo
  5. customthe residue was purified by trituration with Methyl tertiary butyl ether (25 mL)
  6. customto give
  7. filtrationafter filtration a yellow solid (786 mg, 79%)

Quellen und Nachweise

ORD-Eintrag
ord-5a29e04a06ab4bbe94ffec267b460806
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450346B2

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