Sodium hydride → N1-methyl-5-(2-amino-5-cyano-4-pyridyl)oxy-1H-1-indolecarboxamide

HRID 2376917Notes

Reaction equation

HRID 2376917 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[H-].[Na+].[CH2:22]([NH:25][C:26](=O)[O:27]C1C=CC=CC=1)CC.[Cl-].[NH4+]>CN(C)C=O>[CH3:22][NH:25][C:26]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][C:8]3[C:5]([C:6]#[N:7])=[CH:4][N:3]=[C:2]([NH2:1])[CH:9]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)=[O:27]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11252326Carbamic acid, propyl-, phenyl esterHCID 219493966-Amino-4-(1H-5-indolyloxy)nicotinonitrile

Product 1

HCID 21949164N1-methyl-5-(2-amino-5-cyano-4-pyridyl)oxy-1H-1-indolecarboxamideYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Amino-4-(1H-5-indolyloxy)nicotinonitrile (63 mg, 0.252 mmol) was dissolved in N,N-dimethylformamide (1 ml); and sodium hydride (60% in oil, 11.6 mg, 0.29 mmol) was gradually added thereto while stirring at room temperature. After the reaction mixture was stirred for 30 minutes, phenyl N-propylcarbamate (49.5 mg, 0.277 mmol) was added thereto; and the reaction mixture was stirred for 3 hours. A saturated aqueous solution of ammonium chloride was added thereto; this was subjected to extraction with ethyl acetate, and dried over anhydrous sodium sulfate. This solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol) to yield the title compound (12 mg) and N1-methyl-5-(2-amino-5-cyano-4-pyridyl)oxy-1H-1-indolecarboxamide (17 mg).

Workup

  1. stirringAfter the reaction mixture was stirred for 30 minutes
  2. stirringand the reaction mixture was stirred for 3 hours
  3. extractionthis was subjected to extraction with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThis solution was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol)

Sources & evidence

ORD record
ord-38df84226070485bba5df3b9f7697357
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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