352695-78-4Relevant articles and documents
New building blocks for fluorinated imidazole derivatives: Preparation of β-fluoro- and β,β-difluorohistamine
Dolensky,Kirk
, p. 4687 - 4691 (2007/10/03)
We demonstrate that "FBr" addition to 1-trityl-4-vinyl-1H-imidazole (7) provides a convenient route to side-chain-fluorinated histamines. Thus, addition of "FBr" to the double bond of 7 occurs with Markovnikov regioselectivity to produce 4-(2-bromo-1-fluoroethyl)-1-trityl-1H-imidazole (8). Substitution with azide, reduction, and removal of the trityl group provide β-fluorohistamine (1) as the dihydrochloride. Elimination of HBr from 8 followed by a second addition of "FBr" gives 4-(2-bromo-1,1-difluoroethyl)-1-trityl-1H-imidazole (15). This was similarly converted to β,β-difluorohistamine (2) as the dihydrochloride.