Trimethylsilylacetylene → 2-(4-Chloro-2-methylphenyl)-5-trimethylsilanylethynylpyrazine

HRID 734887Notes

Reaction equation

HRID 734887 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][C:11](I)=[CH:10][N:9]=2)=[C:4]([CH3:15])[CH:3]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][C:11]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:10][N:9]=2)=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 860769782-(4-Chloro-2-methylphenyl)-5-iodopyrazine

Product 1

HCID 690630692-(4-Chloro-2-methylphenyl)-5-trimethylsilanylethynylpyrazine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product was prepared analogously to Example 48.1c from 1.70 g (5.14 mmol) of 2-(4-chloro-2-methylphenyl)-5-iodopyrazine and 0.80 mL (5.66 mmol) of trimethylsilylacetylene (using triethylamine as base). Yield: 700 mg (45% of theoretical); C16H17ClN2Si (M=300.858); calc.: molpeak (M+H)+:301/303 (Cl); found: molpeak (M+H)+:301/303 (Cl); Rf value: 0.5 (silica gel, PE/EtOAc 9:1).

Sources & evidence

ORD record
ord-2a42b89c40474d81b60473bd42b4f197
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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