Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N,N-Dimethylethylenediamine | HCID 66053 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 21864764 | HCID 21864764 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | HCID 66893928 | HCID 66893928 | 44% |
Reaction Steps
Xylene (75 mL) was added to 7-iodo-5-nitro-1-benzofuran (1.00 g, 3.46 mmol), N,N-dimethylethane-1,2-diamine (0.37 g, 4.15 mmol), Pd2(dba)3 (0.08 g, 0.87 mmol), Xantphos (0.20 g, 0.35 mmol) and Cs2CO3 (1.59 g, 4.84 mmol). The mixture was stirred at 120° C. overnight, filtered through Celite and the solvent was removed in vacuo. The crude product was purified by flash chromatography [eluent: DCM:MeOH (6:1) and DCM:MeOH:Et3N (9:1:0.1)] to afford 0.378 g (44%) of the title compound. HPLC 90%, RT: 1.430 (System A; 10-97% MeCN over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 2.44 (d, J=3.22 Hz, 6H) 2.81 (t, J=6.56 Hz, 2H) 3.52 (t, J=6.56 Hz, 2H) 6.97 (d, J=2.23 Hz, 1H) 7.40 (d, J=2.23 Hz, 1H) 7.89 (t, J=1.98 Hz, 2H). LC-MS 250 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07820675B2 |
|---|
| Source dataset | uspto-grants-2010_10 |
|---|
| ORD ID | ord-dfe7f7782502427c94741fe658e539f4 |
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| Source note | uspto-grants-2010_10 |
|---|
