Triethylamine → 3-oxo-2-[2-(pyridin-2-ylamino)-ethyl]2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester

HRID 2218938Notes

Reaction equation

HRID 2218938 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:13]=[CH:12][C:11]([CH2:14]CBr)=[C:6]([C:7]([O:9]C)=O)[CH:5]=1.CCN(CC)CC.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][CH2:32][CH2:33][NH2:34]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:14][N:34]([CH2:33][CH2:32][NH:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=1)[C:7]2=[O:9])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 537536654-Bromoethyl-isophthalic acid dimethylester

Product 1

HCID 691775523-oxo-2-[2-(pyridin-2-ylamino)-ethyl]2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (5) (511 mg, 1.78 mmol) in toluene (10 ml) was treated with Et3N (744 μl 5.33 mmol) and N1-pyridin-2-yl-ethane-1,2-diamine (244 mg, 1.78 mmol) [prepared by treatment of 2-bromopyridine with excess ethylene diamine and pyridine] and the mixture refluxed for 6 hours. After cooling to room temperature and evaporation of the solvent, the residue was purified by flash chromatography: silica, CH2Cl2/acetone (3:2).

Workup

  1. temperaturethe mixture refluxed for 6 hours
  2. customevaporation of the solvent
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9e49783638b348db9a9cbd204ad87817
Source dataset
uspto-grants-2008_08
Patent number
US07413727B2

Reaction notes

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