2-Fluorobenzoyl chloride → o-Fluorobenzaldehyde
Reaction equation
ClC1C=CC(C2SC(C3C=CC=CC=3OC(F)F)NN=2)=CC=1.CCN(C(C)C)C(C)C.[F:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>>[F:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[CH:35]=[O:36]Participants
4
Procedure
To the solution of 5-(4-chloro-phenyl)-2-(2-difluoromethoxy-phenyl)-2,3-dihydro-[1,3,4]thiadiazole is added DIEA (0.16 mmol) and 2-fluorobenzoyl chloride (0.16 mmol) and the reaction mixture is stirred for 12 hours at room temperature. After evaporation of the solvent, the residue is purified by automated chromatography (hexane/EtOAc) to give 5-(4-chloro-phenyl)-2-(2-difluoromethoxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2-fluoro-phenyl)-methanone: 1H NMR (400 MHz, CDCl3) δ 7.39-7.35 (m, 1H), 7.34-7.29 (m, 4H), 7.25 (dd, J1=7.8 Hz, J2=1.2 Hz, 1H), 7.19-7.13 (m, 3H), 7.04 (m, 1H), 6.97 (m, 2H), 6.50 (dd, J1=71.6 Hz, J2=71.2 Hz, 1H). LC/MS: (ES+) 462.8 (M+1)+.
Workup
- customAfter evaporation of the solvent
- customthe residue is purified by automated chromatography (hexane/EtOAc)
Sources & evidence
- ORD record
- ord-df3c81162f1144cc8b55ae7bec9d99f9
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569345B2
Reaction notes
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