Trimethylsilylacetylene → 1-benzyl-4-ethynyl-1H-pyrazole

HRID 1042563Notes

Reaction equation

HRID 1042563 reaction equation
C(N1C=C(I)C=N1)C1C=CC=CC=1.[C:14]([C:16]1[CH:17]=[N:18][N:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25](OC)=[CH:24][CH:23]=2)[CH:20]=1)#[CH:15].C[Si](C#C)(C)C>>[CH2:21]([N:19]1[CH:20]=[C:16]([C:14]#[CH:15])[CH:17]=[N:18]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 37945791-Benzyl-4-iodo-1H-pyrazoleHCID 574219374-Ethynyl-1-(4-methoxybenzyl)-1H-pyrazole

Product 1

HCID 574219391-benzyl-4-ethynyl-1H-pyrazoleYield 83%

Procedure

This compound was prepared from 1-benzyl-4-iodo-1H-pyrazole using a similar procedure to that employed in the preparation of 4-ethynyl-1-(4-methoxy-benzyl)-1H-pyrazole (see a)(ii) above). The reaction time was extended to 5 h and 1.6 equivalents of trimethylsilylacetylene were added. Silica-gel flash chromatography of the crude reaction mixture afforded the product as a white solid (83% yield over two steps).

Workup

  1. customSilica-gel flash chromatography of the crude reaction mixture

Sources & evidence

ORD record
ord-5627b99511164e6db8bfc80cb2481444
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

Loading…