Sodium hydride → 2-Methyl-7-azaindole

HRID 427218

Reaction equation

HRID 427218 reaction equation
[C:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][N:6]=1)(=O)[CH3:2].[H-].[Na+]>CNC1C=CC=CC=1>[CH3:2][C:1]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 2682952-Acetamido-3-methylpyridine

Product 1

HCID 5830662-Methyl-7-azaindoleYield 23%

Reagents, catalysts & solvents 1

HCID 7515N-MethylanilineSolvent

Procedure

2-methyl-7-azaindole was prepared in two steps. First, 2-amino-3-picoline was reacted with acetyl chloride in toluene in the presence of pyridine to produce 2-acetamido-3-picoline in 65% yield. Second, pyrolysis of 2-acetamido-3-picoline in N-methylaniline in the presence of NaH at 280° C. was performed to produce 2-methyl-7-azaindole (FIG. 18) in 23% yield. This compound was characterized by NMR spectroscopy.

Workup

  1. customat 280° C.

Sources & evidence

ORD record
ord-0c5ad8252efe4c95b85a7ae974ce9b90
Source dataset
uspto-grants-2001_11
Patent number
US06312835B1

Linked notes

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