Dimethylformamide → Tert-butyl 4-phenyl-2-(6-phenylpyridine-3-carboxamido)benzoate

HRID 454731

Reaktionsgleichung

Reaktionsgleichung von HRID 454731
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[C:12]1([C:18]2[N:23]=[CH:22][C:21]([C:24]([OH:26])=O)=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH2:27][C:28]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:37][C:29]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>C(Cl)Cl.C(N(CC)CC)C>[C:41]1([C:39]2[CH:38]=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])=[C:28]([NH:27][C:24]([C:21]3[CH:22]=[N:23][C:18]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:19][CH:20]=3)=[O:26])[CH:40]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1201186-Phenylnicotinic acidHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Produkt 1

HCID 58508784Tert-butyl 4-phenyl-2-(6-phenylpyridine-3-carboxamido)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

N,N-Dimethylformamide (0.9 μl) and oxalyl chloride (0.023 mL) were added to a methylene chloride (0.5 mL) suspension of 6-phenylpyridine-3-carboxylic acid (44 mg) at room temperature, followed by stirring at the same temperature for 1 hour. The reaction mixture was added to a solution mixture of tert-butyl 2-amino-4-phenylbenzoate (40 mg) in methylene chloride (1 mL) and triethylamine (0.17 mL) at room temperature, followed by stirring at same temperature for 1 hour. The solvent was evaporated under reduced pressure, and ethyl acetate and a 10% aqueous solution of citric acid were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Trikonex AB, FlashTube 2008, eluent: hexane/ethyl acetate=2:1] to obtain tert-butyl 4-phenyl-2-(6-phenylpyridine-3-carboxamido)benzoate.

Aufarbeitung

  1. stirringby stirring at same temperature for 1 hour
  2. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  3. additiona 10% aqueous solution of citric acid were added to the residue
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [Trikonex AB, FlashTube 2008, eluent: hexane/ethyl acetate=2:1]

Quellen und Nachweise

ORD-Eintrag
ord-b23b938d89394061a5e26b7d882a9d40
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492582B2

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