Trimethylsilylacetylene → 6-(4-Chloro-phenyl)-8-methyl-3-trimethylsilanylethynyl-imidazo[1,2-a]pyridine

HRID 558597Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH3:18])[C:11]3[N:12]([C:14](I)=[CH:15][N:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH3:18])[C:11]3[N:12]([C:14]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])=[CH:15][N:16]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 670006486-(4-Chloro-phenyl)-3-iodo-8-methyl-imidazo[1,2-a]pyridine

Product 1

HCID 670001186-(4-Chloro-phenyl)-8-methyl-3-trimethylsilanylethynyl-imidazo[1,2-a]pyridineYield 80%

Procedure

Prepared from 6-(4-chloro-phenyl)-3-iodo-8-methyl-imidazo[1,2-a]pyridine (example C.21 step 2) (3.686 g, 10 mmol) and trimethylsilylacetylene (2.8 mL, 20 mmol) as described in example C.20 step 4. Obtained the title compound as a yellow foam (2.70 g, 80%). MS (ISP) 339.1 [(M+H)+], 341 [(M+2+H)+].

Sources & evidence

ORD record: ord-ad5c866aa499450191c2f19cebf02dc7
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063048B2

Reaction notes

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