5-phenyl-2-(4-trimethylsilanyl-but-3-ynyl)-2H-pyrazole → 2-but-3-ynyl-5-phenyl-2H-pyrazole

HRID 1189151Notes

Reaction equation

HRID 1189151 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][CH2:13][C:14]#[C:15][Si](C)(C)C)[N:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1([C:26]2[CH:27]=[CH:28][N:29]([CH2:31][CH2:32][C:33]#[C:34][Si](C)(C)C)[N:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:31]([N:29]1[CH:28]=[CH:27][C:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:30]1)[CH2:32][C:33]#[CH:34].[CH2:12]([N:11]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]=[N:10]1)[CH2:13][C:14]#[CH:15]

Participants

4

Reactant 2

HCID 665980525-phenyl-2-(4-trimethylsilanyl-but-3-ynyl)-2H-pyrazoleHCID 665984445-phenyl-1-(4-trimethylsilanyl-but-3-ynyl)-1H-pyrazole

Product 2

HCID 860867401-but-3-ynyl-5-phenyl-1H-pyrazoleYield 6%HCID 860867412-but-3-ynyl-5-phenyl-2H-pyrazoleYield 13%

Procedure

The title compounds were prepared in accordance with the general method of Example 108(B), from 5-phenyl-1-(4-trimethylsilanyl-but-3-ynyl)-1H-pyrazole and 5-phenyl-2-(4-trimethylsilanyl-but-3-ynyl)-2H-pyrazole (300 mg, 1.12 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 29 mg (0.15 mmol, 13%) of 2-but-3-ynyl-5-phenyl-2H-pyrazole and 13 mg (66 mmol, 6%) of 1-but-3-ynyl-5-phenyl-1H-pyrazole.

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)

Sources & evidence

ORD record
ord-d1dc72c7390b44e89885c7d373e97bd1
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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