Tri-o-tolylphosphine → Indole naphthyridinone 32

HRID 1362141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362141
[CH3:1][N:2]([CH2:7][C:8]1[C:16]2[C:11](=[C:12]([CH3:17])[CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:18])[C:9]=1[CH3:19])[C:3](=[O:6])[CH:4]=[CH2:5].Br[C:21]1[CH:22]=[C:23]2[C:28](=[N:29][CH:30]=1)[NH:27][C:26](=[O:31])[CH2:25][CH2:24]2.CCN(C(C)C)C(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][N:2]([CH2:7][C:8]1[C:16]2[C:11](=[C:12]([CH3:17])[CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:18])[C:9]=1[CH3:19])[C:3](=[O:6])/[CH:4]=[CH:5]/[C:21]1[CH:30]=[N:29][C:28]2[NH:27][C:26](=[O:31])[CH2:25][CH2:24][C:23]=2[CH:22]=1

Komponenten

7

Edukt 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 110963256-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-oneHCID 66905360N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide

Produkt 1

HCID 6539899Indole naphthyridinone 32Ausbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7854PropionitrileLösungsmittel

Versuchsvorschrift

A mixture of N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide (256 mg, 1 mmole) and 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (227 mg, 1 mmole) in propionitrile (20 mL) was treated with DIEA (0.3 mL), Pd(OAc)2 (29 mg, 0.13 mmole), and tri-o-tolylphosphine (50 mg, 0.16 mmole). The reaction was heated at reflux under argon for 10 h, then was cooled to RT and filtered through supercel. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel to afford the title compound (100 mg, 25%) as an off-white solid: MS (ES) m/e 403.2 (M+H)+. Anal. Calcd for C24H26N4O2.2.75H2O: C, 63.77; H, 7.02; N, 12.39. Found: C, 63.81; H, 7.25; N, 11.90.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux under argon for 10 h
  3. filtrationfiltered through supercel
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-25a8ca842aa34bbaaaf4ccea9a56ccca
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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