Potassium Bicarbonate → HCID 178424921, compound

HRID 1895997Notes

Reaction equation

HRID 1895997 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.Br[C:18]1[NH:22][C:21]([CH3:23])=[N:20][C:19]=1[N+:24]([O-:26])=[O:25].C(=O)(O)[O-].[K+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:18]3[NH:22][C:21]([CH3:23])=[N:20][C:19]=3[N+:24]([O-:26])=[O:25])[CH2:15][CH2:16]2)[N:3]=1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridineHCID 178433401HCID 178433401, compound

Product 1

HCID 178424921HCID 178424921, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A well homogenised mixture of the Compound of Example 3 (100 mg, 0.47 mmol), 5-bromo-2-methyl-4-nitro-1H-imidazole (97 mg, 0.47 mmol) and potassium bicarbonate was stirred at 120° C. for 8 h. The reaction mixture was poured into water and extracted with EtOAc The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by automated flash liquid chromatography (Horizon™-Biotage), eluting with Petroleum Ether-EtOAc 7:3, affording the title product as a brown solid.

Workup

  1. stirringwas stirred at 120° C. for 8 h
  2. extractionextracted with EtOAc The combined organic layers
  3. washwere washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  8. washeluting with Petroleum Ether-EtOAc 7:3

Sources & evidence

ORD record
ord-5a646392d9ba4fafb7130371d83058e2
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…