HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 58896987, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Bromo-6-fluoropyridine | HCID 639438 | — |
| Reactant | 1-Tosyl-1H-pyrrolo(2,3-B)pyridine-4-boronic acid pinacol ester | HCID 49758926 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58896987 | HCID 58896987 | — |
Reaction Steps
In a 20 mL microwave tube, 2-Bromo-6-fluoropyridine (L) (682 mg, 3.3 mmol, 1.2 equiv.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (B)(1.1 g, 2.8 mmol, 1 equiv.) and Pd(PPh3)4 (323 mg, 0.28 mmol), 0.1 equiv.) were suspended in a mixture of DME (10 mL) and aqueous Na2CO3 2M (3 mL). The container was sealed and the reaction mixture was exposed to microwave irradiation for 30 min at 160° C. The resulting mixture was diluted in ethyl acetate, washed with water and dried over anhydrous Na2SO4. The crude material was purified by flash chromatography on silica gel, eluting with hexanes/ethyl acetate mixtures (90:10 to 60:40). The title compound J was isolated as a pale yellow solid (2.1 g, 50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08921376B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-e48bd947ca6846f395da73726199c45e |
| Source note | uspto-grants-2014_12 |