Ethyl orthoformate → 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester

HRID 371920Notes

Reaction equation

HRID 371920 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]([NH:14][CH3:15])=[C:10]([NH2:13])[C:11]=1[Cl:12])=[O:5])[CH3:2].[CH2:17](OC(OCC)OCC)C>>[CH2:1]([O:3][C:4]([C:6]1[C:11]([Cl:12])=[C:10]2[N:13]=[CH:15][N:14]([CH3:17])[C:9]2=[N:8][C:7]=1[CH3:16])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 123876175-Amino-6-methylamino-4-chloro-2-methylpyridine-3-carboxylic acid ethyl ester

Product 1

HCID 123876407-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester

Procedure

2.4 g. of 5-Amino-6-methylamino-4-chloro-2-methylpyridine-3-carboxylic acid ethyl ester (0.01 mol.) and 10 ml. of orthoformic acid triethyl ester are refluxed for 12 hours. After the excess ortho ester has been removed, the residue is recrystallized from ethyl acetate to obtain 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester, m.p. 56°-58°. Yield 2.2 g. (88%).

Workup

  1. customAfter the excess ortho ester has been removed
  2. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8f0db467ef234e229b9b6f21ecf1c85f
Source dataset
uspto-grants-1978_05
Patent number
US04088654

Reaction notes

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