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Imidazole → HCID 72203008, Verbindung

HRID 629057
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 629057
I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CS(C)=O>[N:22]1([C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[O:6])[CH:26]=[CH:25][N:24]=[CH:23]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 26782663-iodo-N-(4-(trifluoromethoxy)phenyl)benzamide

Produkt 1

HCID 72203008HCID 72203008, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3-Iodo-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 1.1, 204 mg, 0.5 mmol), 1H-imidazole (68.1 mg, 1 mmol), CuI (9.52 mg, 0.050 mmol), L-proline (11.51 mg, 0.100 mmol), K2CO3 (138 mg, 1.000 mmol) and DMSO (500 μL) were added to a vial, which was sealed, evacuated/purged with argon and the RM stirred at 90° C. for 70 h. The RM was diluted with DCM/EtOAc, filtered and stirred with of Chelex® 100 (950 mg). The mixture was washed with sat. aq. Na2CO3, brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 12 g, DCM/MeOH+1% NH4OH from 2% B to 10% MeOH+1% NH4OH) to afford the title compound as an off white powder. UPLC-MS (Condition 1) tR=1.55 min, m/z=348 [M+H]+, m/z=346.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.16 (s, 1H) 7.40 (d, J=8.8 Hz, 2H) 7.69 (t, J=7.9 Hz, 1H) 7.85-7.93 (m, 2H) 7.90 (d, J=9.0 Hz, 3H) 8.18 (s, 1H) 8.37 (s, 1H) 10.52 (s, 1H).

Aufarbeitung

  1. customwas sealed
  2. customevacuated/purged with argon
  3. additionThe RM was diluted with DCM/EtOAc
  4. filtrationfiltered
  5. stirringstirred with of Chelex® 100 (950 mg)
  6. washThe mixture was washed with sat. aq. Na2CO3, brine
  7. dry with materialdried over MgSO4
  8. customthe solvent was evaporated off under reduced pressure
  9. customto give the crude product which
  10. customwas purified by flash chromatography (Silica gel column, 12 g, DCM/MeOH+1% NH4OH from 2% B to 10% MeOH+1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-21c8283ee76e4f5dbf05c2ee839f51a4
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315489B2

Notizen zur Reaktion

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