HCID 10387575, compound → HCID 10042197, compound

HRID 2221502Notes

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.FC1C=CC(OCC2C3C=NC(C(OCC)=O)=CC=3N(CC)C=2)=CC=1.[F:57][C:58]1[CH:59]=[CH:60][C:61]([OH:81])=[C:62]([CH:80]=1)[CH2:63][C:64]1[C:68]2[CH:69]=[N:70][C:71]([C:73]([O:75]CC)=O)=[CH:72][C:67]=2[N:66]([CH2:78][CH3:79])[CH:65]=1>>[F:57][C:58]1[CH:59]=[CH:60][C:61]([OH:81])=[C:62]([CH:80]=1)[CH2:63][C:64]1[C:68]2[CH:69]=[N:70][C:71]([C:73]([NH:21][OH:22])=[O:75])=[CH:72][C:67]=2[N:66]([CH2:78][CH3:79])[CH:65]=1

Participants

Reactant 3

HCID 10387575HCID 10387575, compound

HCID 21892192HCID 21892192, compound

HCID 21892228HCID 21892228, compound

Product 1

HCID 10042197HCID 10042197, compound

Procedure

Ethyl 3-(5-fluoro-2-hydroxybenzyl)-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 methods similar to that set forth in Example 55. (b) 3-(5-Fluoro-2-hydroxybenzyl)-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-4cba45f3ae2f457299fc69ce3b334542
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368571B2

Reaction notes

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