Ammonium Hydroxide → 5-(3,4-dimethoxyphenyl)-4-[(4-methyl-1H-indol-7-yl)amino]nicotinonitrile

HRID 506197Notes

Reaction equation

HRID 506197 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([C:18]=2Cl)[C:16]#[N:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:20][C:21]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]2[C:22]=1[CH:23]=[CH:24][NH:25]2.[NH4+].[OH-]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([C:18]=2[NH:30][C:27]2[CH:28]=[CH:29][C:21]([CH3:20])=[C:22]3[C:26]=2[NH:25][CH:24]=[CH:23]3)[C:16]#[N:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 251297854-Chloro-5-(3,4-dimethoxyphenyl)nicotinonitrileHCID 450789374-methyl-1H-indol-7-amine

Product 1

HCID 684659965-(3,4-dimethoxyphenyl)-4-[(4-methyl-1H-indol-7-yl)amino]nicotinonitrileYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(3,4-dimethoxyphenyl)-4-chloronicotinonitrile (120 mg, 0.44 mmol) and 4-methyl-7-aminoindole (77.8 mg, 0.52 mmol) in ethanol (2.5 mL) was heated at the reflux temperature for 24 h and cooled to room temperature. The reaction mixture was treated with aqueous NH4OH and concentrated in vacuo, and the residue was purified by flash column chromatography (ethyl acetate/CH2Cl2 5% to 25%) to provide a 48 mg (29%) of 5-(3,4-dimethoxyphenyl)-4-[(4-methyl-1H-indol-7-yl)amino]nicotinonitrile 530 as an off white solid. HPLC retention time: 9.0 min.(g); MS: 385.3 (M+H); and HRMS: 385.1659.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by flash column chromatography (ethyl acetate/CH2Cl2 5% to 25%)

Sources & evidence

ORD record
ord-e360c1a8cb774d07b2a9f5c5f8329466
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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