HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dodecane → 3-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(3-methyl-pyrazol-1-yl)-pyridin-2-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dodecane | HCID 8182 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Cyclohexane-1,1-diamine | HCID 17842493 | — |
| Reactant | 3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amine | HCID 21111395 | — |
| Reactant | HCID 178428694 | HCID 178428694 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 3-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(3-methyl-pyrazol-1-yl)-pyridin-2-ylamine | HCID 11545390 | 34.2% |
Reaction Steps
To a stirred solution of 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-iodo-pyridin-2-ylamine (100 mg, 0.23 mmol) and 3-methyl-1H-pyrazole (59 mg, 0.70 mmol) in DMSO (1 mL was added K3PO4 (101 mg, 0.47 mmol), dodecane (0.015 mL, 0.05 mmol), cyclohexanediamine (0.009 mL, 0.07 mmol) and copper iodide (CuI) (14 mg, 0.07 mmol). The solution was bubbled with nitrogen for 5 minutes, then radiated with microwave at 150° C. for 2 hours, LCMS checked that the reaction was completed, the mixture was purified by prep-HPLC to leave 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(3-methyl-pyrazol-1-yl)-pyridin-2-ylamine (30 mg), yield 34.2%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08785632B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-b61279b153c24578bb2d6a7f9a25341b |
| Source note | uspto-grants-2014_07 |