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21st January 2014 @ 10:25
Osm: OSM-S-1_to_OSM-S-10

OSM-S-2

Context

OSM Series 1

Original Sources

Preparation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (OSM-S-2)

Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-1)

Scale up (3 mmol): Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-2)

Scale up (11 mmol): Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-3)

Scale up (11 mmol): Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-4)

Preparation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (PMY 2-5)

Preparation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde

TCMDC_AP AEW 2-1

Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (AEW 2-2)

Synthesis of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (AEW 2-3)

Biological Evaluation

First Set of Biological Data

Second Analysis of First Set of Compounds (Avery)

Re-evaluation of TCMDC-123794, TCMDC-123812 and others by GSK Tres Cantos

GSK DHODH Assay

Synonyms

PMY 2, AEW 2

CC(N1C2=CC=C(F)C=C2)=C(C=O)C=C1C

InChI=1S/C13H12FNO/c1-9-7-11(8-16)10(2)15(9)13-5-3-12(14)4-6-13/h3-8H,1-2H3

COLPZCHNJIVKMV-UHFFFAOYSA-N

1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde

Literature

Reported here and here and here though data incomplete.

Procedure used for synthesis: http://dx.doi.org/10.1021/jm00098a013 and  http://dx.doi.org/10.1002/cmdc.200600026

See also community suggestion for synthesis advice that was employed.

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Attached Files
OSM-S-2.cdx
OSM-S-2.png