HCID 10387575, compound → HCID 10359198, compound

HRID 2221501Notes

Reaction equation

C(OCC1C2C(=CN=C(C([NH:21][OH:22])=O)C=2)N(CC2C=CC(F)=CC=2F)C=1)C1C=CC=CC=1.[F:32][C:33]1[CH:56]=[CH:55][C:36]([O:37][CH2:38][C:39]2[C:43]3[CH:44]=[N:45][C:46]([C:48]([O:50]CC)=O)=[CH:47][C:42]=3[N:41]([CH2:53][CH3:54])[CH:40]=2)=[CH:35][CH:34]=1.FC1C=CC(O)=C(C=1)CC1C2C=NC(C(OCC)=O)=CC=2N(CC)C=1>>[F:32][C:33]1[CH:56]=[CH:55][C:36]([O:37][CH2:38][C:39]2[C:43]3[CH:44]=[N:45][C:46]([C:48]([NH:21][OH:22])=[O:50])=[CH:47][C:42]=3[N:41]([CH2:53][CH3:54])[CH:40]=2)=[CH:35][CH:34]=1

Participants

Reactant 3

HCID 10387575HCID 10387575, compound

HCID 21892192HCID 21892192, compound

HCID 21892228HCID 21892228, compound

Product 1

HCID 10359198HCID 10359198, compound

Procedure

Ethyl 3-(4-fluoro-phenoxymethyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate. The title compound can be prepared from ethyl 3-hydroxymethyl-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate and 4-fluorophenol using a methods similar to step (e) of Example 54. (b) 3-(4-Fluoro-phenoxymethyl)-1-ethyl-N-hydroxy-1H-pyrrolo[3,2-c]pyridine-6-carboxamide. The title compound can be prepared from the mixture of ethyl 3-(4-fluoro-phenoxymethyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate and ethyl 3-(5-fluoro-2-hydroxy-benzyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate in a manner similar to step (e) of Example 11. Purification by HPLC can provide the pure title compound.

Sources & evidence

ORD record: ord-64622814dcb74a02a7c3fe3838470a8f
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368571B2

Reaction notes

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