Tri-o-tolylphosphine → (E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(2-oxo-1,4-dihydro-2H-pyrido[2,3-d]-1,3-oxazin-6yl)acrylamide

HRID 225937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 225937
[CH3:1][N:2]([CH2:7][C:8]1[N:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3](=[O:6])[CH:4]=[CH2:5].Br[C:19]1[CH:29]=[N:28][C:22]2[NH:23][C:24](=[O:27])[O:25][CH2:26][C:21]=2[CH:20]=1.CCN(C(C)C)C(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]([CH2:7][C:8]1[N:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3](=[O:6])/[CH:4]=[CH:5]/[C:19]1[CH:29]=[N:28][C:22]2[NH:23][C:24](=[O:27])[O:25][CH2:26][C:21]=2[CH:20]=1

Komponenten

7

Edukt 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 159259906-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-oneHCID 20752825N-Methyl-N-[(1-methyl-2-indolyl)methyl]acrylamide

Produkt 1

HCID 9821027(E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(2-oxo-1,4-dihydro-2H-pyrido[2,3-d]-1,3-oxazin-6yl)acrylamideAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7854PropionitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (1.19 g, 5.2 mmole) in propionitrile (50 mL) was added 6-bromo-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]-1,3-oxazine (1.1 g, 4.9 mmole), DIEA (1.75 mL, 10 mmole), palladium(II) acetate (112 mg, 0.5 mmole), and tri-o-tolylphosphine (304 mg, 1.0 mmole). The reaction was purged with argon and heated at reflux for 16 hr, then was cooled to RT and concentrated under vacuum. The residue was taken up in CHCl3 and the solution was filtered through a pad of silica gel (3% methanol/CHCl3). The filtrate was concentrated and the residue was triturated with ethyl acetate, collected by suction filtration, and dried under vacuum gave the title compound (1.02 g, 55%) as an off-white solid: LCMS (ES) m/e 377 4 (M+H)+.

Aufarbeitung

  1. customThe reaction was purged with argon
  2. temperatureheated
  3. temperatureat reflux for 16 hr
  4. concentrationconcentrated under vacuum
  5. filtrationthe solution was filtered through a pad of silica gel (3% methanol/CHCl3)
  6. concentrationThe filtrate was concentrated
  7. customthe residue was triturated with ethyl acetate
  8. filtrationcollected by suction filtration
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-68de3b63945347abbf8dde52864f6a2c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557125B2

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