Dimethylformamide → N1,3-Dimethyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide

HRID 2215563Notes

Reaction equation

HRID 2215563 reaction equation
[CH3:1][NH:2][C:3](=O)[O:4]C1C=CC=CC=1.[CH3:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[CH:24]=3)[CH:20]=2)[NH:15][CH:14]=1.[H-].[Na+].CN(C)C=O>O>[CH3:1][NH:2][C:3]([N:15]1[C:16]2[C:21](=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[CH:24]=3)=[CH:18][CH:17]=2)[C:13]([CH3:12])=[CH:14]1)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 16034Phenyl MethylcarbamateHCID 24758Sodium hydrideHCID 219492824-(3-Methyl-1H-5-indolyl)oxy-2-pyridinamine

Product 1

HCID 21949213N1,3-Dimethyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamideYield 58.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenyl N-methylcarbamate (350 mg, Production example 2-1) was added to a solution of 4-(3-methyl-1H-5-indolyl)oxy-2-pyridinamine (500 mg), sodium hydride (93 mg) and N,N-dimethylformamide (5 ml) at room temperature; and the reaction mixture was stirred for 2 hours and 45 minutes. Water was added to the reaction mixture; extraction was performed with ethyl acetate; and purification was performed by NH-silica gel column chromatography (Fuji Silysia, hexane:ethyl acetate=1:2, sequentially, ethyl acetate) to yield the title compound as a pale yellow amorphous solid (365 mg).

Workup

  1. extractionextraction
  2. customand purification

Sources & evidence

ORD record
ord-c366face41344ba383514b5435e315a3
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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