Phosphorus oxychloride → 4-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][NH:9][C:5]2=[N+:6]([O-])[CH:7]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[CH:11][C:4]=12

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178526273HCID 178526273, compound

Product 1

HCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

Procedure

4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine can be obtained as in example 4 stage 4(b) but starting from 1.7 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine 7-oxide in 10 cm3 of phosphorus oxychloride. In this way, 1.3 g of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine is obtained as a solid with the following characteristics:

Sources & evidence

ORD record: ord-bba8f1fc49fe4e189565ea6513710e81
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786114B2

Reaction notes

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