HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → HCID 10938089, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Benzyl acrylate | HCID 75617 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-Butyl 6-bromo-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate | HCID 11833959 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | HCID 10938089 | HCID 10938089 | 54% |
Reaction Steps
A solution of 1-(tert-butoxycarbonyl)-6-bromo-1,2,3,4-tetrahydro-1,8-naphthyridine (1.79 g, 5.70 mmole), benzyl acrylate (1.11 g, 6.84 mmole), Pd(OAc)2 (65 mg, 0.29 mmole), P(o-tolyl)3 (173 mg, 0.57 mmole), and (i-Pr)2NEt (2.5 mL, 14.25 mmole) in propionitrile (30 mL) was degassed (3×N2/vacuum) then heated to reflux. After 18 hr the mixture was cooled to RT and concentrated. Flash chromatography on silica gel (25% EtOAc/hexanes) gave the title compound (1.21 g, 54%) as a yellow solid:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07557125B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-7210270071164b9382258bea601f0d7d |
| Source note | uspto-grants-2009_07 |