Trifluoroacetic anhydride → 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]-5-cyanopyridine

HRID 1455994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455994
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:19]([CH:33]=1)[CH2:20][N:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([NH2:32])=O)=[CH:26][N:25]=1)[CH2:22][CH3:23]>N1C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:19]([CH:33]=1)[CH2:20][N:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:32])=[CH:26][N:25]=1)[CH2:22][CH3:23]

Komponenten

6

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 221056502-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxamide

Produkt 1

HCID 221056452-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]-5-cyanopyridineAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trifluoroacetic anhydride (0.51 ml) was added dropwise to a mixture of 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxamide (1.05 g) in pyridine (0.58 ml) and THF (20 ml) at 20° C. The mixture was stirred at ambient temperature for 18 hours, diluted with ethyl acetate, washed with water, saturated aqueous NaHCO3 and brine, and dried (MgSO4). The solvent was evaporated and the residue purified by MPLC, eluting with dichloromethane/methanol mixtures (100:0 to 95:5) to give 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]-5-cyanopyridine (0.81 g) as a gum.

Aufarbeitung

  1. washwashed with water, saturated aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customthe residue purified by MPLC
  5. washeluting with dichloromethane/methanol mixtures (100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-d00d01872da44982a41d6751e17fb0a6
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843942

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