1,3,5-Trimethylpyrazole-4-boronic acid → tert-butyl[2-{[3-(propylsulfonyl)phenyl]ethynyl}-4-(1,3,5-trimethyl-1H-pyrazol-4-yl)phenoxy]acetate
Reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:31][N:32]1[C:36]([CH3:37])=[C:35](B(O)O)[C:34]([CH3:41])=[N:33]1>>[C:1]([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:35]2[C:34]([CH3:41])=[N:33][N:32]([CH3:31])[C:36]=2[CH3:37])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[CH:19]=1)([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
Following the general method as outlined in Intermediate 192, starting from tert-butyl(4-bromo-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate (Intermediate 191) and 1,3,5-trimethyl-1H-pyrazole-4-boronic acid, pinacol ester, the title compound was obtained as a black sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.
Sources & evidence
- ORD record
- ord-360b1f1ec3d649e79aa700f9a102ae11
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273769B2
Reaction notes
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