Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-Chloro-N-methoxy-N-methylisonicotinamide | HCID 18506894 | — |
| Reactant | Tert-butylcarbamate | HCID 21252905 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 18506862 | HCID 18506862 | — |
Reaction Steps
To a solution of 2-chloro-N-methoxy-N-methylisonicotinamide (16-1, 500 mg, 2.49 mmole) in dry dioxane (5 mL) was added Cs2CO3 (1.22 g, 3.74 mmole), Xanthphos (216 mg, 0.37 mmole (Kranenburg, M. et. al. Organometallics 1995, 14, 3081-3089)), Pd2(dba)3 (114 mg, 0.12 mmole), and tert-butylcarbamate (350 mg, 2.99 mmole) then the mixture was heated to reflux. After 18 hr the mixture was cooled to RT., diluted with H2O, and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (50% EtOAc/hexanes) gave the titled compound as a pale yellow solid. 1H-NMR (500 MHz, CDCl3) δ 8.31 (d, 1 H, J=5.13 Hz), 8.16 (bs, 1 H), 7.74 (s, 1 H), 7.12 (d, 1 H, J=5.13 Hz), 3.61 (s, 3 H), 3.34 (s, 3 H), 1.53 (s, 9 H); MS (ES) (M+H)+ 282.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06586424B2 |
|---|
| Source dataset | uspto-grants-2003_07 |
|---|
| ORD ID | ord-8c5ac3ee9e0c4dad8b9cc6573c8b3e5d |
|---|
| Source note | uspto-grants-2003_07 |
|---|
