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

HRID 1293719Notes

Reaction equation

I[C:2]1[N:6]2[CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([C:26]#[C:25][Si:22]([CH3:24])([CH3:23])[CH3:21])=[CH:3][N:4]=3)[CH:7]=2)=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 670004923-Iodo-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

Product 1

HCID 670008776-(4-Trifluoromethyl-phenyl)-3-trimethylsilanylethynyl-imidazo[1,2-a]pyridineYield 89%

Procedure

Prepared from 3-iodo-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine (example C.24 step 2) (2.3 g, 6 mmol) and trimethylsilylacetylene (1.64 mL, 12 mmol) as described in example C.20 step 4. Obtained the title compound as a yellow solid (1.9 g, 89%). MS (ISP) 359.1 [(M+H)+].

Sources & evidence

ORD record: ord-8e43b57445f44e13aa7894b615fdc718
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238808B2

Reaction notes

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