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HCID 68485937, Verbindung → HCID 68485225, Verbindung

HRID 1874903
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1874903
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17](Br)[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[CH2:21]([Zn]CC)[CH3:22]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([CH2:21][CH3:22])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 68485937HCID 68485937, VerbindungHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 68485225HCID 68485225, VerbindungAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (0.400 g, 1.125 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.130 g, 0.112 mmol) were combined in THF (7 mL) and treated with diethylzinc (1 M in heptane) (2.250 mL, 2.250 mmol) with stirring under an inert atmosphere. The reaction mixture was heated to 70° C. and stirred for 2 h. The reaction mixture was concentrated to dryness and partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was isolated, dried over MgSO4, filtered and concentrated to dryness. The residue was purified on 40 g silica gel eluted successively with EtOAc and 10% CH3OH/DCM to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-ethylbenzonitrile (0.213 g, 0.699 mmol, 62.1% yield) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.44-7.54 (m, 3H), 7.12-7.20 (m, 2H), 3.76 (s, 2H), 2.64 (q, J=7.60 Hz, 2H), 1.90 (br. s., 2H), 1.15 (t, J=7.55 Hz, 3H). LC-MS (ES−) m/z 303.25, 305.16 [M−1]. LC-MS (ES+) m/z 305.01, 306.98 [M+H].

Aufarbeitung

  1. stirringstirred for 2 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. custompartitioned between EtOAc and saturated aqueous NaHCO3
  4. customThe organic phase was isolated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified on 40 g silica gel
  9. washeluted successively with EtOAc and 10% CH3OH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-499ad5c78fa041e3b018e84baed0320a
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304419B2

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