Sodium hydride → 2-Phenyl-1H-pyrrolo(2,3-b)pyridine

HRID 427216Notes

Reaction equation

HRID 427216 reaction equation
[C:1]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CNC1C=CC=CC=1>[C:2]1([C:1]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 90211Benzamide, N-(3-methyl-2-pyridyl)-

Product 1

HCID 6066822-Phenyl-1H-pyrrolo(2,3-b)pyridineYield 58%

Reagents, catalysts & solvents 1

HCID 7515N-MethylanilineSolvent

Procedure

2-phenyl-7-azaindole was prepared in two steps. First, 2-amino-3-picoline was reacted with benzoyl chloride in chloroform in the presence of pyridine to produce 2-benzamido-3-picoline in 33% yield. Second, pyrolysis of 2-benzamido-3-picoline in N-methylaniline in the presence of NaH at 280° C. was performed to produce 2-phenyl-7-azaindole (FIG. 18) in 58% yield. This compound was characterized by NMR spectroscopy.

Workup

  1. customat 280° C.

Sources & evidence

ORD record
ord-5de8c0134ad04307a307de38830eb606
Source dataset
uspto-grants-2001_11
Patent number
US06312835B1

Reaction notes

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