HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-(methylsulfonylmethyl)cyclohexanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| 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 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-(methylsulfonylmethyl)cyclohexanol | HCID 86762731 | — |
Reaction Steps
AlMe3, [Rh2(cod)2Cl2], (S)-BINAP, THF, 0° C.; (b) TBSCl, imidazole, DMAP, DMF; (c) 3-chloroperoxybenzoic acid, CH2Cl2; (d) sodium azide, NH4Cl, MeOH, H2Ol; (e) H2, Pd—C (10%), EtOAc; (f) 5-chloro-3-(5-fluoro-4-(methylsulfinyl)pyrimidin-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine, iPr2NEt, microwave, 70° C.; (g) TBAF, THF
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08829007B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-16e1e161550c47389fac1658b23cab04 |
| Source note | uspto-grants-2014_09 |