HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tert-butyl 2-(6-(4-bromophenyl)pyridin-3-yl)propan-2-ylcarbamate | HCID 89462588 | — |
| Reactant | HCID 178476833 | HCID 178476833 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamate | HCID 89463030 | 92.4% |
Reaction Steps
To a solution of tert-butyl 2-(6-(4-bromophenyl)pyridin-3-yl)propan-2-ylcarbamate, 33-f, (850 mg, 2.17 mmol) in toluene (15 ml) was added diethyl phosphonate (900 mg, 6.52 mmol) and Et3N (660 mg, 6.52 mmol) and PdCl2(dppf) (85 mg) under N2, and the reaction mixture was refluxed for 8 hours. The reaction solution was then evaporated and diluted with EtOAc. The organic phase was washed with brine, dried and concentrated. Purified by silica gel (DCM-DCM:MeOH=50:1) to give tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamate (900 mg, 92.4%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09079930B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-23a5d268f39c4186a9b296484f4e5728 |
| Source note | uspto-grants-2015_07 |