HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → 4-[5-Amino-2-(2,4-difluorophenoxy)phenyl]-2-methyl-2,7-naphthyridin-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(2,4-Difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 89657613 | — |
| Reactant | 4-Bromo-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one | HCID 118022083 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-[5-Amino-2-(2,4-difluorophenoxy)phenyl]-2-methyl-2,7-naphthyridin-1-one | HCID 118021727 | 53.1% |
Reaction Steps
For 5 min, N2 was bubbled through a mixture of 4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (64.8 mg, 0.187 mmol), the title compound of Example 51, step 2 (30.0 mg, 0.124 mmol), K2CO3 (51.6 mg, 0.374 mmol) and Pd(dppf)Cl2 (18.3 mg, 0.025 mmol) in dioxane (2.0 mL) and water (0.2 mL) which was then microwaved at 100° C. for 1 h. Purification by preparative TLC (DCM:MeOH=20:1, Rf=0.5) gave the title compound (25.0 mg, 53%) as yellow gum. LCMS: 380.0 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09034900B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-2f7095a51b5b40728ed8c39bc8d2e76a |
| Source note | uspto-grants-2015_05 |