1,2-Dichloroethane → 3-Pyridinecarboxamide, N-[4-(2-methyl-1H-indol-1-yl)phenyl]-

HRID 275785Notes

Reaction equation

HRID 275785 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:17])=[CH:4][CH:3]=1.[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.C(Cl)CCl>C(#N)C.O>[CH3:17][C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:18]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[O:25])=[CH:3][CH:4]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 938Nicotinic AcidHCID 15549846HCID 15549846, compound

Product 1

HCID 97974473-Pyridinecarboxamide, N-[4-(2-methyl-1H-indol-1-yl)phenyl]-Yield 33.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of the above amine (0.08 g, 0.36 mmol), nicotinic acid (114 mg, 0.59 mmol) and EDC (66 mg, 0.54 mmol) was dissolved in 2 mL acetonitrile and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, extracted with EtOAc, washed with water and dried (MgSO4). The residue obtained on concentration was flash chromatographed on silica gel, eluting with a gradient of 2% MeOH in dichloromethane to give the title compound (40 mg).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customThe residue obtained on concentration
  5. customchromatographed on silica gel
  6. washeluting with a gradient of 2% MeOH in dichloromethane

Sources & evidence

ORD record
ord-4a93c74852714413929ac3f26a073378
Source dataset
uspto-grants-2002_03
Patent number
US06353007B1

Reaction notes

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