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Dimethylformamide → HCID 69085234, Verbindung

HRID 2362467
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2362467
Cl[C:2]1[N:7]=[CH:6][C:5]([C@@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[O:11][C:10](=[O:20])[NH:9]2)=[CH:4][CH:3]=1.[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)#[CH:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.CN(C)C=[O:60]>[Pd](Cl)Cl.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.[Cu]I>[C:12]([O-:11])(=[O:60])[CH3:13].[NH4+:7].[F:19][C:15]1[CH:14]=[C:13]([C@H:12]2[O:11][C:10](=[O:20])[NH:9][C@@H:8]2[C:5]2[CH:6]=[N:7][C:2]([C:22]#[C:21][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:3][CH:4]=2)[CH:18]=[CH:17][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 6228DimethylformamideHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 86673453HCID 86673453, Verbindung

Produkt 2

HCID 517165Ammonium Acetate
HCID 69085234
HCID 69085234, Verbindung
Ausbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator

Versuchsvorschrift

(4R,5R)-4-(6-chloropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one (52 mg; 0.18 mmol), ethynylbenzene (20.0 mg, 0.19 mmol), bis(triphenylphosphine) palladium (II) chloride (6.2 mg, 8.88 μmol), triphenylphosphine (9.3 mg, 0.036 mmol), and copper (I) iodide (1.6 mg, 8.88 μmol) were combined in a microwave vial. dimethylformamide (0.5 mL) and diisopropylethylamine (1.5 mL) were added resulting in a biphasic mixture. Nitrogen was bubbled through the vessel for 10 min, the vessel was capped and the reaction was run at 120° C. for 25 min on a Biotage microwave reactor. The diisopropylethylamine removed in vacuo, the remaining solution was diluted with methanol and the solution was purified via preparative liquid chromatography (Sunfire C18 OBD 30×100 mm 5 μm, A=95% H2O/5% Acetonitrile, B=95% Acetonitrile/5% H2O, Modifier 10 mM Ammonium Acetate, 0.00 min=20% B, 10.0 min=100% B, 15.0 min=100% B, Flow rate=40 mL/min) providing 31 mg (48%) (4R,5R)-5-(3-fluorophenyl)-4-(6-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ ppm 8.49 (1H, d, J=2.14 Hz), 7.75 (1H, dd, J=8.24, 2.44 Hz), 7.56-7.66 (3H, m), 7.32-7.46 (4H, m), 7.11 (1H, td, J=8.39, 2.44 Hz), 6.98-7.09 (2H, m), 5.34 (1H, s), 5.28 (1H, d, J=7.63 Hz), 4.79 (1H, d, J=7.32 Hz). Mass Spectral Anal. Calcd. for [M+H]+ C22H15FN2O2: 359.1. found 359.3.

Aufarbeitung

  1. customresulting in a biphasic mixture
  2. customNitrogen was bubbled through the vessel for 10 min
  3. customthe vessel was capped
  4. customThe diisopropylethylamine removed in vacuo
  5. additionthe remaining solution was diluted with methanol
  6. customthe solution was purified via preparative liquid chromatography (Sunfire C18 OBD 30×100 mm 5 μm

Quellen und Nachweise

ORD-Eintrag
ord-1ea56a06b6a146f48d413d31e83e4e50
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691821B2

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