Trimethylsilylacetylene → HCID 42645334, compound

HRID 1669883Notes

Reaction equation

HRID 1669883 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:12]=[C:13]([N:15]=[N+:16]=[N-:17])[CH:14]=1)=[O:8])[CH3:5].[C:25]([Si](C)(C)C)#[CH:26]>CN(C=O)C>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[CH:12]=[C:13]([N:15]2[CH:26]=[CH:25][N:17]=[N:16]2)[CH:14]=1)=[O:8])[CH3:5]

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 57770821HCID 57770821, compound

Product 1

HCID 42645334HCID 42645334, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-azido-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (488 mg, 1.5 mmol), ethynyltrimethylsilane (4.5 mmol, 0.64 mL) in DMF (6 mL) was heated to 110° C. for 16 hours. The mixture was cooled and filtered, and the filtrate was purified by preparative HPLC to afford 262 mg of 4′-methyl-5-[1,2,3]triazol-1-yl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide as white solid (50%). MS (M+H)=351.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-053de94d9f5b422b804d75031c4ca6ed
Source dataset
uspto-grants-2011_08
Patent number
US07989637B2

Reaction notes

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