Toluene → HCID 86623338, compound

HRID 912562Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14](O)=[O:15])=[C:9]2[CH3:17])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:31])=O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]([Cl:31])=[O:15])=[C:9]2[CH3:17])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1

Participants

Conditions

Temperature: 1.5 °C

Procedure

To a suspension of 1-(4-fluoro-2-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole-3-carboxylic acid (0.65 g, 2.16 mmol) in anhyd toluene (5.0 mL) cooled to 0-3° C. were added thionyl chloride (0.25 mL) and DMF (20 μL). The reaction mixture was allowed to warm to room temperature where it remained for 3 h and then was concentrated in vacuo. The residue was evaporated twice from 5 mL of toluene to remove thionyl chloride and then was triturated in 3 mL of hexanes. The solids were removed by filtration and the filtrate was concentrated under reduced pressure and dried under high vacuum to afford the title compound (0.44 g, 64%) as a pale brown solid; 1H NMR (CDCl3): δ 7.59 (dd, J=8, 3 Hz, 1H), 7.44 (m, 1H), 7.27 (dd, J=5, 8 Hz, 1H), 6.51 (s, 1H), 2.17 (s, 3H), 1.89 (s, 3H); MS (ESI) m/z 320 [M+H]+.

Workup

temperatureto warm to room temperature where it
concentrationwas concentrated in vacuo
customThe residue was evaporated twice from 5 mL of toluene
customto remove thionyl chloride
customwas triturated in 3 mL of hexanes
customThe solids were removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customdried under high vacuum

Sources & evidence

ORD record: ord-875e0cdef6bd4a91aef3f0ff04f18e8e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026237B2

Reaction notes

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