Nitrogen → (E)-3-[4(tert-Butoxycarbonyl)-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-7-yl]acrylic acid

HRID 18219

Reaktionsgleichung

Reaktionsgleichung von HRID 18219
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C:10]2[CH:14]=[C:15](Br)[CH:16]=[N:17][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]([O:23]CC1C=CC=CC=1)(=[O:22])[CH:20]=[CH2:21].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(C(C)C)C(C)C.N#N>C(#N)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C:10]2[CH:14]=[C:15](/[CH:21]=[CH:20]/[C:19]([OH:23])=[O:22])[CH:16]=[N:17][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 5

HCID 947NitrogenHCID 75617Benzyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 22139026tert-butyl 7-bromo-2H,3H,4H-pyrido[3,2-b][1,4]oxazine-4-carboxylate

Produkt 1

HCID 22139159(E)-3-[4(tert-Butoxycarbonyl)-3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-7-yl]acrylic acidAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7854PropionitrileLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  1. temperaturethen heated to reflux
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-14a4e5731d124901879b83d5e2acd1fd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

Verknüpfte Notizen

Wird geladen…