Methanol → 5-(4-Cyano-2-nitrophenyl)amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole

HRID 1419163Notes

Reaction equation

HRID 1419163 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=1.Cl[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34].C(N(CC)CC)C.CO>C(O)C.C(Cl)Cl>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[C:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=2)=[C:26]([N+:33]([O-:35])=[O:34])[CH:27]=1)#[N:30]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 543263845-amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole

Product 1

HCID 538656485-(4-Cyano-2-nitrophenyl)amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indoleYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-Amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole and 4-chloro-3-nitrobenzonitrile were used. Triethylamine was used as base, absolute ethanol was used as solvent, and the reaction was heated at reflux for 2 hours. Column chromatography using 1% methanol in methylene chloride afforded the title compound (40%) as a red foam: mp, decomposes 85° C.; Rf =0.35 in 1% methanol in methylene chloride; HRMS calculated for C25H25N5O4 459.1909, found 459.1853.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-b3eadea9002549f2b546fe4bf1b97743
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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