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HCID 54263873, Verbindung → HCID 22918525, Verbindung

HRID 2380019
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2380019
Cl[C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:12][C:11]=2[O:21][CH3:22])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(P([Ni-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>[CH3:22][O:21][C:11]1[CH:12]=[CH:13][C:14]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:15][C:10]=1[CH2:9][NH:8][C:7]1[C:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:3][CH:4]=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 54263873HCID 54263873, VerbindungHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 22918525HCID 22918525, VerbindungAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479587HCID 178479587, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

To a 250mL 3 neck round bottom flask equipped with a mechanical stirrer, thermometer, addition funnel, and nitrogen inlet, were charged 98.1 mL of tetrahydrofuran, 3.27 grams (9.83 mmoles) of the 2-chloro-3-(2-methoxy-5trifluoromethoxybenzylamino) pyridine and 1.93 grams (2.95 mmoles) of bis(triphenylphosphino)nickel(II) chloride. The black reaction mixture was stirred at 25 degree celsius for 40 minutes. Phenylmagnesium bromide (1M/THF, 38.4 mL, 38.4 mmoles) was added over a 25 minute period and the resulting black slurry was stirred for 2 hours at 25 degree celsius. During this time, the reaction was monitored by thin layer chromatography assay. The reaction mixture was cooled to 4° C., and quenched with 5.89 mL acetic acid. The reaction mixture was vacuum concentrated to a low volume and partitioned between 100 mL each of toluene and water. The organic layer was washed several times with water and concentrated to an oil. The oil was purifid by column chromatography to yield 1.88 grams (51.1%) of the desired material (as an oil). The structure of this compound was assigned on the basis of high resolution NMR. 1H NMR (CDCl3) 8.05 (d, 1H), 7.63 (d, 2H), 7.45 (m, 3H), 7.12 (bs, 1H), 7.08 (m, 2H), 6.93 (dd, 1H), 6.85 (d, 1H), 4.71 (t, 1H), 4.26 (d, 2H), 3.78 (s, 3H).

Aufarbeitung

  1. additionthermometer, addition funnel, and nitrogen inlet
  2. customThe black reaction mixture
  3. stirringthe resulting black slurry was stirred for 2 hours at 25 degree celsius
  4. customquenched with 5.89 mL acetic acid
  5. concentrationconcentrated to a low volume
  6. custompartitioned between 100 mL each of toluene and water
  7. washThe organic layer was washed several times with water
  8. concentrationconcentrated to an oil

Quellen und Nachweise

ORD-Eintrag
ord-ebbbc4db2b22443d91da8a8f489376df
Quelldatensatz
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05364943

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