HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Diethyl (5-{[(tert-butoxycarbonyl)amino](phenyl)methyl}pyridin-2-yl)phosphonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethylphosphite | HCID 3780918 | — |
| Reactant | tert-Butyl[(6-bromopyridin-3-yl)(phenyl)methyl]carbamate | HCID 131733138 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Diethyl (5-{[(tert-butoxycarbonyl)amino](phenyl)methyl}pyridin-2-yl)phosphonate | HCID 131733137 | 86% |
Reaction Steps
To tert-butyl (6-bromopyridin-3-yl)(phenyl)methylcarbamate (4-e) (3.4 g, 9.4 mmol), diethyl phosphite (1.55 g, 11.27 mmol) and Et3N (1.14 g, 11.27 mmol) in THF was added PdCl2(dppf) (200 mg). The mixture was heated at reflux under nitrogen overnight. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified over silica gel (DCM/MeOH=20/1) to provide the product, 4-f (3.4 g, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09079930B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-5ef3b9b7d63240faab60b022c60e09a2 |
| Source note | uspto-grants-2015_07 |