HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 90417433, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester | HCID 11218053 | — |
| Reactant | Methyl 6-chloropyridazine-3-carboxylate | HCID 12379801 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90417433 | HCID 90417433 | 79.2% |
Reaction Steps
Methyl 6-chloropyridazine-3-carboxylate (1.00 g, 5.79 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1.22 g, 5.79 mmol), Pd(PPh3)4 (536 mg, 0.44 mmol) and Cs2CO3 (3.40 g, 10.4 mmol) were suspended in dioxane (8 mL) and water (8 mL) and heated in a microwave reactor at 125° C. for 30 min. 1M aq HCl (10 mL) was added, the precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was passed through a silica pad eluting with 30% MeOH in DCM and concentrated in vacuo to give the title compound as a white solid (946 mg, 79.2%). LCMS (ES+): 207.1 [MH]+. HPLC: Rt 3.30 min, 49.9% purity.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09428498B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-c3eb75805b934c7dba8ff3f9dd3aa768 |
| Source note | uspto-grants-2016_08 |