Pyridine → 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine

HRID 427754Notes

Reaction equation

HRID 427754 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([NH2:19])=O)=[CH:13][N:12]=1)[CH2:9][CH3:10].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:19])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 183577602-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide

Product 1

HCID 183577802-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridineYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide (example 4) (1.93 g, 5.5 mmol) was suspended in THF (30 ml) and treated with pyridine (1.15 g, 14.25 mmol, 1.15 ml) followed by trifluoroacetic anhydride (3.4 g, 16 mmol) whilst stirring at ambient temperature. The white solid dissolved and there was a slight exotherm. The resultant solution was left overnight at ambient temperature. The mixture was then evaporated to low volume, a saturated aqueous solution of sodium bicarbonate was added and the mixture stirred at ambient temperature for 30 minutes. The mixture was again evaporated to low volume and the white solid that precipitated was filtered, washed with water and sucked dry (1.68 g). The solid was purified by MPLC on silica to give 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine as a white solid (1.15 g, 63%).

Workup

  1. dissolutionThe white solid dissolved
  2. customThe mixture was then evaporated to low volume
  3. additiona saturated aqueous solution of sodium bicarbonate was added
  4. stirringthe mixture stirred at ambient temperature for 30 minutes
  5. customThe mixture was again evaporated to low volume
  6. customthe white solid that precipitated
  7. filtrationwas filtered
  8. washwashed with water
  9. customsucked dry (1.68 g)
  10. customThe solid was purified by MPLC on silica

Sources & evidence

ORD record
ord-964c3fbe30444177b0588093a0cf6655
Source dataset
uspto-grants-2001_11
Patent number
US06313148B1

Reaction notes

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