HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → 5-bromo-N-(1-cyclohexyl-5-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 1-Cyclohexyl-5-[(piperidin-1-yl)methyl]-1H-benzimidazol-2-amine | HCID 21899178 | — |
| Reactant | 5-Bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole | HCID 58317256 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-bromo-N-(1-cyclohexyl-5-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-amine | HCID 67254403 | 68.1% |
Reaction Steps
A mixture of 1-cyclohexyl-5-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-2-amine (420 mg, 0.00134 mol), 5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (916 mg, 0.00202 mol), xantphos (237 mg, 0.000410 mol), tris(dibenzylideneacetone)dipalladium(0) (147 mg, 0.000160 mol), and potassium phosphate (510 mg, 0.00240 mol) in 1,4-Dioxane (6.0 mL) was flushed with argon. The mixture was microwaved at 300 watts, 130° C. for 15 minutes. The reaction mixture was filtered, concentrated and purified by preparative HPLC to yield 582 mg of 5-bromo-N-(1-cyclohexyl-5-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-amine as the bis-TFA salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08293923B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-677dbb9bd4d6467696cd18dd044b177e |
| Source note | uspto-grants-2012_10 |