HCID 10387575, compound → HCID 10384126, compound

HRID 2221500Notes

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.ClC1C=C(F)C=CC=1OCC1C2C=NC(C(OCC)=O)=CC=2N(CC)C=1.[Cl:58][C:59]1[C:60]([OH:83])=[C:61]([CH:79]=[C:80]([F:82])[CH:81]=1)[CH2:62][C:63]1[C:67]2[CH:68]=[N:69][C:70]([C:72](OCC)=[O:73])=[CH:71][C:66]=2[N:65]([CH2:77][CH3:78])[CH:64]=1>>[Cl:58][C:59]1[C:60]([OH:83])=[C:61]([CH:79]=[C:80]([F:82])[CH:81]=1)[CH2:62][C:63]1[C:67]2[CH:68]=[N:69][C:70]([C:72]([NH:21][OH:22])=[O:73])=[CH:71][C:66]=2[N:65]([CH2:77][CH3:78])[CH:64]=1

Participants

Reactant 3

HCID 10387575HCID 10387575, compound

HCID 21892203HCID 21892203, compound

HCID 21892229HCID 21892229, compound

Product 1

HCID 10384126HCID 10384126, compound

Procedure

Ethyl 3-(3-chloro-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 2-chloro-4-fluorophenol using methods similar to that set forth in Example 55. (b) 3-(3-Chloro-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-(2-chloro-4-fluoro-phenoxymethyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate and ethyl 3-(3-chloro-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-3b92ebf1577546a4b61498755a0c50c4
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368571B2

Reaction notes

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