HuagongsheHuagongshe Chemistry Print Report · For research reference only
6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(3,2-b)pyridine → 5-(4-(methylsulfonyl)benzyl)-2-(1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(3,2-b)pyridine | HCID 24229270 | — |
| Reactant | 2-Chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine | HCID 86670092 | — |
| 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 | 5-(4-(methylsulfonyl)benzyl)-2-(1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine | HCID 60198094 | — |
Reaction Steps
The title compound was prepared in a manner similar to EXAMPLE 3 using 2-chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x9, 50 mg, 0.127 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[3,2-b]pyridine (61.8 mg, 0.253 mmol) and PdCl2(dppf) (4.63 mg, 6.33 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.03-3.18 (m, 1 H), 3.18-3.30 (m, 5 H), 3.73-3.87 (m, 2 H), 3.92-4.19 (m, 3 H), 4.59-4.81 (m, 3 H), 6.76-6.97 (m, 1 H), 7.53-7.77 (m, 2 H), 7.86-8.08 (m, 2 H), 8.14-8.33 (m, 1 H), 8.96-9.20 (m, 1 H), 9.26-9.42 (m, 1 H), 12.40-12.69 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O3S, 477.16; found 477.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09045496B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-787fce41e9824a61a4eaedb4acba89ba |
| Source note | uspto-grants-2015_06 |