Pyridine → 6-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine

HRID 1870771Notes

Reaction equation

HRID 1870771 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[N:16]=[N:15][C:14]([C:17]([NH2:19])=O)=[CH:13][CH: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[N:16]=[N:15][C:14]([C:17]#[N:19])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 186932416-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide

Product 1

HCID 226225146-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The phenol from the previous step (1.73 g, 4.9 mmol) in THF (30 ml) was treated with pyridine (0.82 ml, 0.82 g, 10.2 mmol) followed by trifluoroacetic anhydride (1.61 ml, 2.42 g, 11.5 mmol). The mixture turned dark green and was left overnight at ambient temperature. The mixture was then evaporated to a gum, treated with an excess of an aqueous solution of sodium bicarbonate and stirred at ambient temperature for approximately 30 minutes. The resultant red solid was filtered, washed with water and sucked dry (1.8 g) and purified by MPLC to give 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine (as a white solid (0.87 g, 53%).

Workup

  1. customThe mixture was then evaporated to a gum
  2. additiontreated with an excess of an aqueous solution of sodium bicarbonate
  3. filtrationThe resultant red solid was filtered
  4. washwashed with water
  5. customsucked dry (1.8 g)
  6. custompurified by MPLC

Sources & evidence

ORD record
ord-32b819612ff54f16a31f323145559fb9
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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