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Cesium carbonate → Ethyl (2-fluoro-4-((4-fluorobenzyl)amino)-6-nitrophenyl)carbamate

HRID 1404832
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1404832
C(OC([N:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10](Br)=[CH:9][C:8]=1[F:17])=O)C.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:17][C:8]1[CH:9]=[C:10]([NH:29][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=2)[CH:11]=[C:12]([N+:13]([O-:15])=[O:14])[C:7]=1[NH:6][C:18](=[O:19])[O:20][CH2:21][CH3:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 673264-FluorobenzylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86700476HCID 86700476, Verbindung

Produkt 1

HCID 86700477Ethyl (2-fluoro-4-((4-fluorobenzyl)amino)-6-nitrophenyl)carbamateAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of compound 2 (0.300 g, 0.790 mmol, 1.00 equiv) in 1,4-dioxane (10 mL) were added 4-fluorobenzylamine (0.200 g, 1.58 mmol, 2.00 equiv), Cs2CO3 (0.500 g, 1.50 mmol, 2.00 equiv) followed by Pd2 (dba)3 (0.072 g, 0.079 mmol, 10 mol %) and Xantphos (0.045 g, 0.079 mmol, 10 mol %) at RT. The reaction mixture was heated at 90° C. and stirred at the same temperature for 8 h. After consumption of the starting material (by TLC), the reaction mixture was concentrated under vacuum. The obtained residue was diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The crude material was purified by silica gel column chromatography (EtOAc/Hexane 2:23) to afford compound 3 (0.140 g, 50.3%) as yellow solid. TLC: 40% EtOAc/Hexane (Rf: 0.25); 1H NMR (500 MHz, CDCl3): δ 7.31-7.28 (m, 2H), 7.06 (t, J=8.5 Hz, 1H), 7.00 (s, 2H), 6.91 (br s, 1H), 6.60 (d, J=9.5 Hz, 1H), 4.46 (br s, 1H), 4.31 (d, J=4.4 Hz, 2H), 4.20 (q, J=7.0 Hz, 2H), 1.28 (t, J=7.0 Hz, 3H); LC-MS: m/z=350 (M+-1) at RT 3.69 (97.8% purity).

Aufarbeitung

  1. customAfter consumption of the starting material (by TLC)
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. additionThe obtained residue was diluted with water (50 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude material was purified by silica gel column chromatography (EtOAc/Hexane 2:23)

Quellen und Nachweise

ORD-Eintrag
ord-910ca26a52e14e46b9855c2a1062f5e1
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08916133B2

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