HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester → [2-(4-Fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)benzoyl]-naphthalen-2-yl ester | HCID 11685250 | — |
| Reactant | HCID 178505764 | HCID 178505764 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | tetrahydrofuran N-methylpyrrolidinone | HCID 22156051 | — |
| Product | [2-(4-Fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone | HCID 10481006 | 78% |
Reaction Steps
Add 4-fluorobenzylzinc chloride (4 mL of 0.5 M/THF) to a stirred solution of trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester (525 mg), Pd(dba)2 (68 mg), dppf (66 mg) and Bu4NI (1.1 g) in THF/NMP (2 mL/1.5 mL) at room temperature. Heat the mixture to reflux for 2 h and quench with water. Dilute the mixture with CH2Cl2 and wash with water and brine, dry over MgSO4, filter and concentrate. Load the crude product on an SCX cartridge, wash with MeOH and elute the product with 2M NH3/MeOH. Purify the product by flash chromatography (0–5% (2M NH3 in MeOH/CH2Cl2) to afford [2-(4-fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (380 mg, 78%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07119206B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-2d5e7b27f2e94b53a9fa0fd7dd229beb |
| Source note | uspto-grants-2006_10 |