Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Methyl 5-formyl-2-(trifluoromethylsulfonyloxy)benzoate | HCID 15466849 | — |
| Reactant | 1-[2-Chloro-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-6H-dibenzo[b,f]azocin-5-yl]-ethanone | HCID 69196384 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 72557543 | HCID 72557543 | 55% |
Reaction Steps
A 15 mL three necked oven dried round bottom flask was cooled under argon and charged with Example 21A (50 mg, 0.12 mmol), Example 236A (47 mg, 0.15 mmol) and toluene (2 mL)/EtOH (1 mL). The mixture was purged with argon for 30 minutes. Pd(PPh3)4 (14 mg, 0.012 mmol) and 2 M Na2CO3 (187 μl, 0.36 mmol were added and the reaction was heated at 75° C. for 2 hours. The resulting mixture was poured into water (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by radial chromatography (2 mm plate, 30% to 50% EtOAc/Hexanes) to give the desired product Example 236B (29 mg, 55%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07417040B2 |
|---|
| Source dataset | uspto-grants-2008_08 |
|---|
| ORD ID | ord-290f2b23488041d693d366ceead89b0b |
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| Source note | uspto-grants-2008_08 |
|---|
