HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → tert-Butyl 4-formyl-6-methoxypyridin-2-ylcarbamate
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-6-methoxypyridine-4-carbaldehyde | HCID 2762976 | — |
| Reactant | Tert-butylcarbamate | HCID 21252905 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | tert-Butyl 4-formyl-6-methoxypyridin-2-ylcarbamate | HCID 18506791 | — |
Reaction Steps
To a solution of 2-chloro-6-methoxyisonicotinaldehyde (15-2, 500 mg, 2.91 mmole) in dry dioxane (5 mL) was added Cs2CO3 (1.42 g, 4.37 mmole), Xanthphos (253 mg, 0.44 mmole), Pd2(dba)3 (133 mg, 0.15 mmole), and tert-butylcarbamate (410 mg, 3.5 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 (gradient, 0-10% EtOAc/hexanes) gave the titled compound as an orange solid. 1H-NMR (500 MHz, CDCl3) δ9.98 (s, 1H), 7.91 (s, 1H), 6.82 (s, 1H), 3.88 (s, 3H), 1.54 (s, 9H); MS (ES) (M+H)+253.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06586423B2 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-1c92b2160d60402aad2a052b60b6c2ff |
| Source note | uspto-grants-2003_07 |