Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Oxygen | HCID 977 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Iodo-5-methoxypyridine | HCID 7010733 | — |
| Reactant | 5-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester | HCID 58824162 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58824205 | HCID 58824205 | 58.5% |
Reaction Steps
A mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (51) (126 mg), 2M aqueous cesium carbonate (0.6 mL) and 2-iodo-5-methoxypyridine (95 mg) in 1,4-dioxan (10 mL) under an argon atmosphere was sonicated to expel traces of oxygen. [1,1′-Bis-(diphenylphoshino)ferrocene]dichloropalladium (II) (8 mg) was added and the mixture heated at 95° C. for 18 hours. After cooling, the mixture was acidified to pH6 with 1M aqueous hydrochloric acid and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give compound 52 as an oil (70 mg), which was used directly in the next step. LC/MS System A: Rt=3.23 mins, m/z=354 ((M+H) for C20H19NO5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07858644B2 |
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| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-fa07e533ffa845a38932f7904345c227 |
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| Source note | uspto-grants-2010_12 |
|---|
