1-Methyl-1H-pyrazole-4-boronic acid → tert-butyl(4-(1-methyl-1H-pyrazol-4-yl)-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate

HRID 2390249Notes

Reaction equation

HRID 2390249 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[CH:36]=[C:35](B(O)O)[CH:34]=[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[CH:34]=[N:33][N:32]([CH3:31])[CH:36]=2)=[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

Reactant 2

HCID 112635011-Methyl-1H-pyrazole-4-boronic acidHCID 56593972Tert-butyl(4-bromo-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate2×

Product 1

HCID 58521937tert-butyl(4-(1-methyl-1H-pyrazol-4-yl)-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetateYield 79%

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-methyl-1H-pyrazole-4-boronic acid, pinacol ester, the title compound was obtained as a yellow sticky solid in 79% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-b2f8f0086f88427aa5cbb7ecae19560a
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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