Triphenylphosphine → 2-Chloro-11-fluoro-5-methyl-5,6-dihydroindolo[2,1-a][2,6]naphthyridine

HRID 595721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595721
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH3:11])[CH2:9]O)=[C:4]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[C:18]([F:21])[CH:17]=[CH:16][CH:15]=3)[CH:3]=1.CCOC(/N=N/C(OCC)=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]([CH3:11])[CH2:9][N:13]3[C:14]4[CH:15]=[CH:16][CH:17]=[C:18]([F:21])[C:19]=4[CH:20]=[C:12]3[C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 903334522-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propan-1-ol

Produkt 1

HCID 903339322-Chloro-11-fluoro-5-methyl-5,6-dihydroindolo[2,1-a][2,6]naphthyridineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 2-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propan-1-ol (60 mg, 0.21 mmol) and DEAD (111 mg, 0.63 mmol) in THF (4 mL) was added PPh3 (156 mg, 0.63 mmol) at 0° C. under N2, and the mixture was stirred for 12 hours. Then the mixture was diluted with H2O and extracted with EA. The combined organic layer was washed with H2O, brine, dried over Na2SO4, filtrated and concentrated to give 2-chloro-11-fluoro-5-methyl-5,6-dihydroindolo[2,1-a][2,6]naphthyridine (30 mg, yield: 56%). 1H-NMR (CDCl3, 400 MHz) δ 8.26 (s, 1H), 7.54 (s, 1H), 7.05˜7.15 (m, 3H), 6.73˜6.77 (m, 1H), 4.16˜4.20 (m, 1H), 4.00˜4.04 (m, 1H), 3.31˜3.35 (m, 1H), 1.30 (d, J=8.0 Hz, 3H). MS (M+H)+: 287/289.

Aufarbeitung

  1. extractionextracted with EA
  2. washThe combined organic layer was washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltrated
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-386637657d9e4263b6658344b4806235
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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