Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 89484872 | HCID 89484872 | — |
| 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 | HCID 71547691 | HCID 71547691 | — |
Reaction Steps
A mixture of tert-butyl (3-(3-chloroquinoxaline-6-carbonyl)-2,4-difluorophenyl) carbonate (60 mg, 0.14 mmol, 1.0 eq.), phenylboronic acid (17 mg, 0.14 mmol, 1.1 eq.), Pd(dppf)2Cl2 (6 mg, 0.007 mmol, 0.05 eq.) and Na2CO3 (30 mg, 0.28 mmol, 2.0 eq.) in dioxane and water (9 mL/1 mL) was heated at 100° C. overnight under N2 protection, then cooled and concentrated. The resulting residue was purified via flash column chromatography (PE/EA=3/1, v/v) to (2,6-difluoro-3-hydroxyphenyl)(3-phenylquinoxalin-6-yl)methanone (15.4 mg, 30%). LRMS (M+H+) m/z calculated 363.1, found 363.0. 1H NMR (CDCl3, 400 MHz) δ 10.38 (s, 1 H), 9.76 (s, 1 H), 8.28-8.40 (m, 5 H), 7.60-7.62 (m, 3 H), 7.18-7.27 (m, 2 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09249111B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-a3474e1ec32a481aa87d70190f91c2fe |
|---|
| Source note | uspto-grants-2016_02 |
|---|
