4-(Hydroxymethyl)benzeneboronic acid → 2-trifluoromethyl-N-{3-[4-(hydroxymethyl)phenyl]pyrazin-2-yl}benzene sulfonamide
Reaction equation
Cl[C:2]1[C:3]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1.[OH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[F:19][C:18]([F:21])([F:20])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:3]1[C:2]([C:27]2[CH:28]=[CH:29][C:24]([CH2:23][OH:22])=[CH:25][CH:26]=2)=[N:7][CH:6]=[CH:5][N:4]=1)(=[O:11])=[O:10]Participants
3
Procedure
Following the general method as outlined for Intermediate 4, starting from N-(3-chloropyrazin-2-yl)-2-(trifluoromethyl)benzenesulfonamide and 4-hydroxymethyl benzene boronic acid, the title compound was isolated, after evaporation and recrystallization, as a yellowish solid in 85% yield (97% purity by HPLC).
Sources & evidence
- ORD record
- ord-d21e7414f2694f60a3680e5c7b993330
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796280B2
Reaction notes
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