Ethanol → HCID 59704769, compound

HRID 389556Notes

Reaction equation

HRID 389556 reaction equation
[Br:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[Br:11].C(N1C=CN=C1)(N1[CH:18]=[CH:17]N=C1)=O.C(O)C>C(#N)C>[CH2:17]([O:9][C:8](=[O:10])[C:7]1[C:2]([Br:1])=[C:3]([Br:11])[CH:4]=[N:5][CH:6]=1)[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 597046094,5-Dibromopyridine-3-carboxylic acid

Product 1

HCID 59704769HCID 59704769, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4,5-dibromonicotinic acid (10 g, 36 mmol) in acetonitrile (160 mL) under nitrogen was treated with 1,1′-carbonyldiimidazole (8.65 g, 53.4 mmol) in portions over 10 min. The resulting mixture was stirred for 3 h at room temperature. Ethanol (24 mL) was added and the mixture was heated to 55° C. for 16 h. The solution was then filtered and the filtrate evaporated in vacuo. The residual oil was dissolved in ethyl acetate and the solution was washed with water followed by brine. The organic fraction was then dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography to afford 9 g (82%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.70 (s, 1H), 8.74 (s, 1H), 4.44 (q, J=7.1 Hz, 2H), 1.42 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturethe mixture was heated to 55° C. for 16 h
  2. filtrationThe solution was then filtered
  3. customthe filtrate evaporated in vacuo
  4. dissolutionThe residual oil was dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. dry with materialThe organic fraction was then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ec308f4f5ceb49b1a1b6be32b9fb1a36
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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