HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 66673662, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 5-bromopyridine-2-carboxylate | HCID 7016458 | — |
| Reactant | HCID 66673217 | HCID 66673217 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66673662 | HCID 66673662 | 76.5% |
Reaction Steps
Combine 2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.351 g, 1.32 mmol) and 5-bromo-pyridine-2-carboxylic acid methyl ester (Song, J.; Yee, N. K. J. Org. Chem. 2001, 66, 605) (0.345 g, 1.59 mmol) in dioxane (20 mL). Treat the solution with Xantphos (38 mg, 0.066 mmol) and Cs2CO3 (0.647 g, 1.97 mmol). Degas the reaction by purging with nitrogen for 5 min. Add Pd2(dba)3 (12 mg, 0.0132 mmol) and reflux the reaction mixture overnight. Dilute with EtOAc (100 mL) and water (100 mL). Collect the insoluble material by filtration. Wash with water (2×20 mL) and EtOAc (2×20 mL) and dry in a vacuum oven to give 0.403 g (76%) of the title compound. LC-MS/ES (35Cl) 399.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101764B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-e6a44b1d9b2c4818b76b6482fe9e1cb8 |
| Source note | uspto-grants-2012_01 |