4-Fluorophenylboronic acid → HCID 86680478, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10](C(=O)C)[N:9]=2)=[CH:4][CH:3]=1.FC1C=CC(B(O)O)=CC=1.[Br:26]C1N=C(Cl)SN=1>>[Br:26][C:10]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[S:12][N:11]=1Participants
Procedure
In another embodiment, 1-(5-(4-fluorophenyl)-1,2,4-thiadiazol-3-yl)ethanone is prepared according to the methodology and reagents of Scheme 17A. Specifically, 4-fluorophenyl boronic acid is reacted with 3-bromo-5-chloro-1,2,4-thiadiazole to provide 3-bromo-5-(4-fluorophenyl)-1,2,4-thiadiazole. 3-Bromo-5-(4-fluorophenyl)-1,2,4-thiadiazole is then reacted with a tin reagent such as tributyl(1-ethoxyvinyl)-stannane to convert the bromide moiety of 3-bromo-5-(4-fluorophenyl)-1,2,4-thiadiazole to an acetyl group. In one embodiment, this reaction is performed in the presence of a catalyst such as PdCl2(PPh3)4. In another embodiment, the reaction is performed in DMF at elevated temperatures overnight. 1-(5-(4-Fluorophenyl)-1,2,4-thiadiazol-3-yl)-ethanone may then converted to a compound of Formula (I-A) by the methods described herein, such as Scheme 1.
Sources & evidence
- ORD record
- ord-35906050557e4c3b84c7b844bf4234e1
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809372B2
Reaction notes
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