HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → (1S,3R)-N1-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N3-(pyrazin-2-yl)cyclohexane-1,3-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | 5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 57597747 | — |
| Reactant | 5-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine | HCID 67285321 | — |
| Reactant | (R)-N-((1R,3S)-3-((2-chloro-5-fluoropyrimidin-4-yl)amino)cyclohexyl)-3-fluoropyrrolidine-1-carboxamide | HCID 86719751 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1S,3R)-N1-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N3-(pyrazin-2-yl)cyclohexane-1,3-diamine | HCID 68008579 | — |
Reaction Steps
NaBH4, MeOH; (b) 5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine, 2-Me-THF, water, K3PO4, Pd(PPh3)4, XPhos, Tris(dibenzylideneacetone)dipalladium, reflux; (c) bis(2,5-dioxopyrrolidin-1-yl) carbonate, iPr2NEt, CH3CN; (d) (3R)-3-fluoropyrrolidine, iPr2NEt, CH3CN (e) 2N LiOH, THF.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08829007B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-6140d402d4e0403a82537d816846490a |
| Source note | uspto-grants-2014_09 |