1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid → 4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 452765Notes

Reaction equation

HRID 452765 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([NH:12][NH2:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[NH:14]1[C:18]2[N:19]=[CH:20][CH:21]=[C:22]([C:23](O)=O)[C:17]=2[CH:16]=[CH:15]1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[O:11][C:23]([C:22]3[CH:21]=[CH:20][N:19]=[C:18]4[NH:14][CH:15]=[CH:16][C:17]=34)=[N:13][N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acidHCID 686637333-(3-Fluorophenyl)propanohydrazide

Product 1

HCID 686630174-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]-1H-pyrrolo[2,3-b]pyridineYield 40%

Procedure

In the same manner as in Example 14 and using 3-(3-fluorophenyl)propanohydrazide instead of 1H-benzotriazole-5-carbohydrazide and 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid instead of 3-(3-cyanophenyl)propionic acid, the title compound (yield 40%) was obtained as pale-yellow crystals.

Sources & evidence

ORD record
ord-8297be140ed34a47bf3843759385546b
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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