HCID 11740236, compound → HCID 9999511, compound

HRID 2221498Notes

Reaction equation

HRID 2221498 reaction equation
C([O:8][NH:9]C(C1N=CC2N(CC3C=CC(F)=CC=3)C=NC=2C=1)=O)C1C=CC=CC=1.[F:29][C:30]1[CH:53]=[C:52]([F:54])[CH:51]=[CH:50][C:31]=1[CH2:32][N:33]1[C:37]2=[CH:38][N:39]=[C:40]([C:42]([OH:44])=O)[CH:41]=[C:36]2[CH:35]=[C:34]1[C:45]([O:47][CH2:48][CH3:49])=[O:46]>>[F:29][C:30]1[CH:53]=[C:52]([F:54])[CH:51]=[CH:50][C:31]=1[CH2:32][N:33]1[C:37]2=[CH:38][N:39]=[C:40]([C:42](=[O:44])[NH:9][OH:8])[CH:41]=[C:36]2[CH:35]=[C:34]1[C:45]([O:47][CH2:48][CH3:49])=[O:46]

Participants

3

Reactant 2

HCID 11740236HCID 11740236, compoundHCID 21892243HCID 21892243, compound

Product 1

HCID 9999511HCID 9999511, compound

Procedure

Ethyl 1-(2,4-difluorobenzyl)-5-formyl-1H-pyrrolo[2,3-c]pyridine-2-carboxyl ate. The title compound can be prepared by alkylation of ethyl 5-formyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (prepared according to J.-F. Rousseau, R. H. Dodd, X. Doisy, P. Potier, Heterocycles 1989, 28, 1101-1113) and 2,4-difluorobenzyl bromide in a manner similar to step (a) in Example 1. (b) 1-(2,4-Difluorobenzyl)-(2-ethoxycarbonyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound can be prepared by oxidation of ethyl 1-(2,4-difluoro-benzyl)-5-formyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate according to the procedure by R. H. Dodd, M. Le Hyaric, Synthesis 1993, 295-287. (c) Ethyl 1-(2,4-Difluorobenzyl)-5-hydroxycarbamoyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate. The title compound can be prepared from 1-(2,4-difluorobenzyl)-(2-ethoxycarbonyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid following in a manner similar to step (c ) in Example 1.

Workup

  1. customLe Hyaric, Synthesis 1993, 295-287

Sources & evidence

ORD record
ord-9a78aa40bed6432ba585bd247bc5799e
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

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