Triethylamine → HCID 22727956, compound

HRID 2086064Notes

Reaction equation

HRID 2086064 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=2)[CH:13]=1.C(N(CC)CC)C>CN1CCCC1=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:14]3[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=3)[CH:19]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4595213-(Pyridin-3-yl)anilineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 22727956HCID 22727956, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-bromo-2-chloro-3-nitropyridine (7.0 g, 29 mmol) and 3-(pyridin-3-yl)phenylamine (5.0 g, 29 mmol) in 1-methyl-2-pyrrolidinone (10 ml) and triethylamine (4 ml, 29 mmol) was heated at 100° C. for 90 minutes. The reaction was cooled, suspended in ethyl acetate (400 ml) and insoluble material removed by filtration. The filtrate was then washed with water, brine and dried over anhydrous sodium sulphate. This solution was filtered and pre-adsorbed on to silica gel. Purification by silica gel chromatography eluting with hexane containing triethyline (1%) on a gradient of ethyl acetate from 20% to 35% gave N-(5-bromo-3-nitropyridin-2-yl)-N-[3-(pyridin-3-yl)phenyl]amine as a red solid (5.1 g, 47%); δH (400 MHz, CDCl3) 7.35-7.45 (2H, m, ArH), 7.51 (1H, t, J 8, ArH), 7.62 (1H, d, J 8, ArH), 7.88-7.91 (2H, m, pyridyl-H and NH), 8.53 (1H, s, pyridyl-H), 8.62 (1H, d, J 5, pyridyl-H), 8.68 (1H, s, pyridyl-H), 9.88 (1H, s, pyridyl-H), 10.14 (1H, s, pyridyl-H); m/z (ES+) 371 and 373 (M++H).

Workup

  1. temperatureThe reaction was cooled
  2. custominsoluble material removed by filtration
  3. washThe filtrate was then washed with water, brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationThis solution was filtered and pre-adsorbed on to silica gel
  6. customPurification by silica gel chromatography
  7. washeluting with hexane
  8. additioncontaining triethyline (1%) on a gradient of ethyl acetate from 20% to 35%

Sources & evidence

ORD record
ord-e0ff21071d8d4f889b223b513a3822e2
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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