HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → (E)-3-[4(tert-Butoxycarbonyl)-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-7-yl]acrylic acid
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 7-bromo-2H,3H,4H-pyrido[3,2-b][1,4]oxazine-4-carboxylate | HCID 22139026 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | (E)-3-[4(tert-Butoxycarbonyl)-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-7-yl]acrylic acid | HCID 22139159 | 94.8% |
Reaction Steps
A solution of 4-(tert-butoxycarbonyl)-7-bromo-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazine (1.27 g, 4.03 mmole), benzyl acrylate (785 mg, 4.84 mmole), Pd(OAc)2 (45 mg, 0.20 mmole), P(o-tolyl)3 (122 mg, 0.4 mmole), and (i-Pr)2NEt (1.76 mL, 10.1 mmole) in propionitrile (20 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 (1.17 g, 73%) as a yellow oil: MS (ES) m/e 397 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07741339B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-14a4e5731d124901879b83d5e2acd1fd |
| Source note | uspto-grants-2010_06 |