Trimethylsilylacetylene → 6-iodo-2-[4-(4-trimethylsilyl-1H-1,2,3,-triazole-1-yl)phenyl]imidazo[1,2-a]pyridine

HRID 1746286Notes

Reaction equation

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

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 867297872-(4-Azidophenyl)-6-iodoimidazo[1,2-a]pyridine

Product 1

HCID 903321716-iodo-2-[4-(4-trimethylsilyl-1H-1,2,3,-triazole-1-yl)phenyl]imidazo[1,2-a]pyridine

Procedure

Then, 6-iodo-2-(4-azidophenyl)imidazo[1,2-a]pyridine as prepared above is allowed to react with trimethylsilyl acetylene to obtain 6-iodo-2-[4-(4-trimethylsilyl-1H-1,2,3,-triazole-1-yl)phenyl]imidazo[1,2-a]pyridine (FIG. 1, step 2) in accordance with known methods (for example, the method described in a literature, James T. Fletcher et al., Tetrahedron Lett, 2008, 49, p. 7030-7032), and then trimethylsilyl group is removed (FIG. 1, step 3), to obtain 6-iodo-2-[4-(1H-1,2,3,-triazole-1-yl)phenyl]imidazo[1,2-a]pyridine.

Sources & evidence

ORD record: ord-6f7c38eb33cf424fad47202596f8e999
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09149546B2

Reaction notes

Loading…