2-(2-Pyridyl)malondialdehyde → HCID 85840646, compound

HRID 2099510Notes

Reaction equation

HRID 2099510 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[N:3]=1.[CH:10]1[CH:15]=[C:14]([CH:16]([CH:19]=O)[CH:17]=O)[N:13]=[CH:12][CH:11]=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:19]=[C:16]([C:14]3[CH:15]=[CH:10][CH:11]=[CH:12][N:13]=3)[CH:17]=[N:9]2)[N:3]=1

Participants

4

Reactant 2

HCID 27372452-(2-Pyridyl)malondialdehydeHCID 193925882-Bromo-6-hydrazinopyridine

Product 1

HCID 85840646HCID 85840646, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2-Bromo-6-hydrazinopyridine (500 mg, 2.7 mmol) was dissolved in ethanol (10 mL) and 2-(2-pyridyl)malondialdehyde(403 mg, 2.7 mmol) was added. The reaction was heated at 70° C. for 16 h. The solvents were removed the ethanol in vacuo and the residue was chromatographed on silica gel eluting with hexanes:EtOAc (1:4) to afford 2-bromo-6-(4-pyridin-2-yl-1H-pyrazol-1-yl)pyridine as a light yellow solid. 1H-NMR (CDCl3, 300 MHz) δ 9.0 (s, 1H), 8.62-8.61 (d, J=3 Hz 1H), 8.27 (s, 1H), 7.97-7.94 (d, J=9 Hz, 1H), 7.74-7.57 (m, 3H), 7.39-7.37 (d, J=3 Hz, 1H) 7.19-7.15 (t, 1H). MS (ESI) 301.0 (M++H), 303.0 (M+H+2).

Workup

  1. customThe solvents were removed the ethanol in vacuo
  2. customthe residue was chromatographed on silica gel eluting with hexanes:EtOAc (1:4)

Sources & evidence

ORD record
ord-5de8595fbf454394a7ae0072aa315ebb
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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