Triphenylphosphine → HCID 12001588, compound

Participants

Reaction Steps

To a mixture of 10g (0.1 g; 0.28 mmol) and PPh3 (0.11 g; 0.43 mmol) in THF (3 ml) was added DIAD (0.09 g; 0.43 mmol) at 0° C. After 5 min. diphenylphosphorylazide (0.12 g; 0.43 mmol) was added and the mixture was allowed to reach room temperature. Stirring was continued for 2 hours. The solvent was removed by evaporation and the residue was eluted through silica gel with a mixture of dichloromethane and methanol (50:1 v/v) to afford 25g. LC-ESI-HRMS of [M+H]+ shows 377.1188 Da. Calc. 377.118455 Da, dev. 0.9 ppm In analogy herewith the following compounds were prepared 5-Azidomethyl-1-[3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-1H-benzoimidazole (25c) from 10c. LC-ESI-HRMS of [M+H]+ shows 375.1671 Da. Calc. 375.168182 Da, dev. −2.9 ppm 5-Azidomethyl-1-[3-(2-methyl-2H-pyrazol-3-ylmethoxymethyl)-phenyl]-1H-benzoimidazole (25e) from 10e. LC-ESI-HRMS of [M+H]+ shows 374.1732 Da. Calc. 374.172925 Da, dev. 0.7 ppm

Provenance & Evidence