Chloride → HCID 15661156, Verbindung

HRID 344962

Reaktionsgleichung

Reaktionsgleichung von HRID 344962
[CH3:1][C:2]1([CH3:17])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([CH3:16])=[C:7]([C:14]#[CH:15])[CH:8]=2)[O:3]1.Cl[C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]=1.[Cl-]>C(N(CC)CC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:26]([O:25][C:23](=[O:24])[C:22]1[CH:28]=[CH:29][C:19]([C:15]#[C:14][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][C:6]=2[CH3:16])[O:3][C:2]([CH3:17])([CH3:1])[CH2:11][C:10]3([CH3:12])[CH3:13])=[N:20][CH:21]=1)[CH3:27]

Komponenten

6

Edukt 3

HCID 312ChlorideHCID 2799611Ethyl 6-chloronicotinate2×HCID 156611392,2,4,4,7-Pentamethyl-6-ethynyl-chroman2×

Produkt 1

HCID 15661156HCID 15661156, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10122028Bis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 300 mg (1.316 mmol) of 2,2,4,4,7-pentamethyl-6-ethynyl-chroman (Compound 9) and 245.6 mg (1.3276 mmol) of ethyl 6-chloro-nicotinate (Compound 98) in 2 ml of triethylamine was placed in a pressure tube and a stream of nitrogen was bubbled through the solution for 15 min. The tube was then flushed with argon and a finely ground mixture 100 mg (0.1425 mmol) of bis (triphenylphosphine) palladium II) chloride and 50 mg (0.2625 mmol) of cuprous iodide was added to the solution. The pressure tube was then sealed and the reaction mixture heated at 60 degrees C. for 72 h. The mixture was cooled to room temperature and the triethylamine removed under vacuum. The residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane) to give the title compound as a yellow solid. PMR (CDCl3): & 1.37 (6H, s), 1.38 (6H, s), 1.44 (3H, t, J~7.2 Hz), 1.85 (2H, s), 2.49 (3H, s), 4.43 (2H, q, J~7.2 Hz), 6.70 (1H, s), 7.55-7.61 (2H, m), 8.28 (1H, dd, J~8.2 Hz, 2.1 Hz), 9.22 (1H, d, J~2.1 Hz). MS exact mass, m/e 377.1982 (calcd. for C24H27O3N, 377.1991).

Aufarbeitung

  1. customa stream of nitrogen was bubbled through the solution for 15 min
  2. customThe tube was then flushed with argon
  3. customThe pressure tube was then sealed
  4. temperatureThe mixture was cooled to room temperature
  5. customthe triethylamine removed under vacuum
  6. customThe residue was purified by flash chromatography (silica; 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-eb5d5c3ab35a46958671ca0355fbeb62
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053523

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