4-methyl-1H-indol-5-amine → 5-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile

HRID 506174Notes

Reaction equation

HRID 506174 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[I:10].[NH2:11][C:12]1[C:13]([CH3:21])=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2>CCO.[O-]S([O-])(=O)=O.[Na+].[Na+]>[I:10][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([C:2]=1[NH:11][C:12]1[C:13]([CH3:21])=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2)[C:8]#[N:9]

Participants

5

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 594311594-Chloro-5-iodonicotinonitrile

Product 1

HCID 684438315-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrileYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24436Sodium SulfateSolvent

Procedure

A mixture of 4-chloro-5-iodonicotinonitrile (5.0 g, 18.9 mmol) and 5-amino-4-methylindole (3.0 g, 20.8 mmol) in EtOH (100 mL) was heated at reflux for 3 days, cooled to r.t. and diluted with saturated aq. Na2SO4 (300 mL). The precipitated solids were collected by filtration, washed with water and dried to give 5.3 g (75%) of 5-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile as a grey solid. Melting range: 192-194° C.; MS (M+H+): 375.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-69d704865e544c8892253cab414e6d75
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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