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

HRID 1455994Notes

Reaction equation

HRID 1455994 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

HCID 221056452-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]-5-cyanopyridineYield 80.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d00d01872da44982a41d6751e17fb0a6
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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