HCID 10387575, compound → HCID 9999511, compound
Reaction equation
C(OC[C:10]1[C:18]2[C:13](=[CH:14][N:15]=[C:16]([C:19]([NH:21][OH:22])=[O:20])[CH:17]=2)[N:12]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])[CH:11]=1)C1C=CC=CC=1.FC1C=C(F)C=CC=1CN1C2=CN=C(C=O)C=C2C=C1[C:47]([O:49][CH2:50][CH3:51])=[O:48]>>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[CH2:23][N:12]1[C:13]2=[CH:14][N:15]=[C:16]([C:19](=[O:20])[NH:21][OH:22])[CH:17]=[C:18]2[CH:10]=[C:11]1[C:47]([O:49][CH2:50][CH3:51])=[O:48]Participants
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.
Sources & evidence
- ORD record
- ord-7f08f5acfafa4b8584eff33f5ae106e1
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368571B2
Reaction notes
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