Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One | HCID 73712352 | — |
| Reactant | HCID 178448254 | HCID 178448254 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 73712337 | HCID 73712337 | 18.8% |
Reaction Steps
Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(dppf)Cl2 (˜5 mol %), and CuI (˜6 mol %) in dry THF (0.5 mL) followed by 2-methylpropyl zinc bromide (0.273 mL, 0.138 mmol (0.5M in THF)) dropwise. The solution was heated in the microwave for 10 minutes at 160° C., filtered, and was purified by Prep HPLC to give 3.6 mg (15%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 417 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm 0.93 (d, 6H), 1.91-2.03 (m, 3H), 2.41 (br d, 2H), 2.58 (d, 2H), 3.23 (br t, 2H), 3.72 (br d, 2H), 3.96 (m, 3H), 5.42 (s, 1H), 6.29-6.40 (m, 1H), 6.95 (d, 1H), 7.24-7.54 (m. 8H), 7.83 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06921821B2 |
|---|
| Source dataset | uspto-grants-2005_07 |
|---|
| ORD ID | ord-52fce34d521a40a5a3c995b6296167a6 |
|---|
| Source note | uspto-grants-2005_07 |
|---|
