Trimethylsilylacetylene → [5-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridin-3-yl]dimethylamine

HRID 734874Notes

Reaction equation

HRID 734874 reaction equation
Br[C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2[CH:6]=[C:7]([N:8]([CH3:10])[CH3:9])[C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[N:3][CH:4]=2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 86076948[2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]dimethylamine

Product 1

HCID 69058189[5-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridin-3-yl]dimethylamine

Procedure

The product was prepared analogously to Example 7.1c starting from [2-bromo-5-(4-chlorophenyl)pyridin-3-yl]dimethylamine and trimethylsilylacetylene. Yield: 0.50 g (quant. yield); C18H21ClN2Si (M=328.911); calc.: molpeak (M+H)+:329/331 (Cl); found: molpeak (M+H)+:329/331 (Cl); HPLC-MS: 7.41 minutes (method B).

Workup

  1. customThe product was prepared analogously to Example 7.1c
  2. custom7.41 minutes (method B)

Sources & evidence

ORD record
ord-7c6719280e8e489d87b94949cfb14547
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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