3-Pyridinecarbonyl Azide → 5-(N,N-Dimethylamino)-1-(3-pyridylcarbamoyl)indoline

HRID 356046Notes

Reaction equation

HRID 356046 reaction equation
[CH3:1][N:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)[CH3:3].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]=[C:20]=[O:21])[CH:14]=1.C(N=[N+]=[N-])(=O)C1C=CC=NC=1>C1(C)C=CC=CC=1>[CH3:3][N:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:20](=[O:21])[NH:19][C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1)[CH2:8][CH2:7]2)[CH3:1]

Participants

5

Reactant 3

HCID 199143-Pyridinecarbonyl AzideHCID 27604933-IsocyanatopyridineHCID 16767807N,N-Dimethylindolin-5-amine

Product 1

HCID 105170195-(N,N-Dimethylamino)-1-(3-pyridylcarbamoyl)indolineYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(N,N-dimethylamino)indoline (D13) (0.29 g, 1.79 mmol) was added to solution of 3-pyridylisocyanate derived from nicotinoyl azide (0.52 g, 1.2 eq) heated at reflux in dry toluene for 1.5 h. The solution was allowed to stand overnight evaporated under reduced pressure and purified by column chromatography (SiO2, CHCl3 /MeOH 2-5%) to afford a pale blue oil which on trituration with Et2O afforded a pale blue solid (550 mg, 99%).

Workup

  1. temperatureheated
  2. customevaporated under reduced pressure
  3. custompurified by column chromatography (SiO2, CHCl3 /MeOH 2-5%)
  4. customto afford a pale blue oil which on trituration with Et2O

Sources & evidence

ORD record
ord-ca083d1be0b14e19b0481e6901607100
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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