Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Nitroaniline | HCID 7423 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Chloropyridine | HCID 12287 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58337727 | HCID 58337727 | 82% |
Reaction Steps
3-nitroaniline (1.82 g, 13.2 mmol, 1.5 eq), 3-chloropyridine (1 g, 8.8 mmol, 1 eq), Cs2CO3 (4.02 g, 12.3 mmol, 1.4 eq), Pd2(dba)3 (403 mg, 0.44 mmol, 0.05 eq) and Xantphos (511 mg, 0.88 mmol, 0.1 eq) were dissolved in toluene (10 mL) in a flame-dried sealed tube and heated at 110° C. for 18 h. The reaction was cooled to rt, diluted with CH2Cl2 and filtered through a plug of celite. Purification by flash chromatography on silica gel afforded 1.55 g (82%) of the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 8.89 (s, 1H), 8.42 (d, J=2.7 Hz, 1H), 8.17 (d, J=4.5, 1H), 7.79 (t, J=2.1 Hz, 1H), 7.64 (d, J=7.7 Hz, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.52-7.45 (m, 2H), 7.33 (dd, J=8.2, 4.6 Hz, 1H); ES-MS [M+1]+: 216.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08501757B2 |
|---|
| Source dataset | uspto-grants-2013_08 |
|---|
| ORD ID | ord-c8179b5d07df48178f58f156b607a09d |
|---|
| Source note | uspto-grants-2013_08 |
|---|
