Methylamine → 5-(2-methylamino-1-phenyl-ethyl)-1H-indole-2-carbonitrile

HRID 268903Notes

Reaction equation

HRID 268903 reaction equation
[C:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13]OS(C)(=O)=O)=[CH:7][CH:6]=2)#[N:2].[CH3:25][NH2:26]>>[CH3:25][NH:26][CH2:13][CH:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3]([C:1]#[N:2])=[CH:11]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86612756methanesulfonic acid 2-(2-cyano-1H-indol-5-yl)-2-phenyl-ethyl ester

Product 1

HCID 598318115-(2-methylamino-1-phenyl-ethyl)-1H-indole-2-carbonitrile

Procedure

A mixture of methanesulfonic acid 2-(2-cyano-1H-indol-5-yl)-2-phenyl-ethyl ester CCLXXI (0.24 g) and a solution of methylamine (33% in EtOH, 15 mL) was heated at reflux for 2 hours. The resulting mixture was evaporated under reduced pressure and the residue was purified by flash chromatography (DCM/(DCM+MeOH+NH4OH 60/10/1), 70/30 to 50/50) to give 80 mg of 5-(2-methylamino-1-phenyl-ethyl)-1H-indole-2-carbonitrile CCLXXII as a light yellow foam. MS=290 [M+H]+.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe resulting mixture was evaporated under reduced pressure
  3. customthe residue was purified by flash chromatography (DCM/(DCM+MeOH+NH4OH 60/10/1), 70/30 to 50/50)

Sources & evidence

ORD record
ord-29ead3da7db64fcfb42c18b28e69c72a
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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