Methylamine → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(methylamino)pyridine-3-carbonitrile

HRID 13815Notes

Reaction equation

HRID 13815 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[N:3]=1.[NH2:24][CH3:25]>>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:4]1[N:3]=[C:2]([NH:24][CH3:25])[C:7]([C:8]#[N:9])=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 102371012-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

Product 1

HCID 687190996-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(methylamino)pyridine-3-carbonitrile

Procedure

To the product of Step C (300 mg) was added H2NCH3 (3.34 mL, 2 M solution in THF). The reaction stirred at room temperature overnight before concentrating. The product was dissolved in EtOAc and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 0% to 20% EtOAc in hexane affording the title compound. HPLC/MS: 353.9 (M+1), 355.9 (M+3); Rt=4.21 min.

Workup

  1. concentrationbefore concentrating
  2. dissolutionThe product was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel with a gradient elution of 0% to 20% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-6580fa0bfeac4e7fad3eaafdcf660b82
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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