HuagongsheHuagongshe Chemistry Print Report · For research reference only
1H-Indole-4-boronic acid → 2-(1H-indol-4-yl)-5-((6-methylpyridin-2-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1H-Indole-4-boronic acid | HCID 2763173 | — |
| Reactant | HCID 86670105 | HCID 86670105 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 2-(1H-indol-4-yl)-5-((6-methylpyridin-2-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine | HCID 60197375 | — |
Reaction Steps
The title compound was prepared in a manner similar to EXAMPLE 3 using 2-chloro-5-((6-methylpyridin-2-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x28, 36 mg, 0.108 mmol), 1H-indol-4-ylboronic acid (34.9 mg, 0.217 mmol) and PdCl2(dppf) (7.94 mg, 10.85 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.50 (s, 3 H), 3.26-3.44 (m, 3 H), 3.54-3.68 (m, 2 H), 3.95-4.06 (m, 1 H), 4.06-4.17 (m, 1 H), 4.55-4.81 (m, 4 H), 6.93-7.05 (m, 1 H), 7.20-7.37 (m, 3 H), 7.54-7.64 (m, 3 H), 7.64-7.70 (m, 1 H), 7.70-7.81 (m, 1 H), 11.47-11.66 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O, 412.20; found 412.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09045496B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-d7a701e5bc384c9398143c9bf82ee736 |
| Source note | uspto-grants-2015_06 |