StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

2-Chloroaniline → HCID 89783333, Verbindung

HRID 1055932
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1055932
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C(=O)=O.CO.CCO.CC(O)C.[NH4+].[OH-]>[Cl:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH:18]=[CH:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 72402-ChloroanilineHCID 2733832Lithium hexamethyldisilazaneHCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Produkt 1

HCID 89783333HCID 89783333, VerbindungAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 280Carbon DioxideLösungsmittel
HCID 702
Ethanol
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 3776IsopropanolLösungsmittel
HCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 53.5 mg, 0.180 mmol), 2-chloroaniline (94 μl, 0.898 mmol), and LHMDS (1.0 M in THF; 898 μl, 0.898 mmol) was stirred in a sealed flask at 65° C. for 4 h. The mixture was then partitioned between DCM (50 mL) and saturated aq. NH4Cl (30 mL). The organic layer was separated, and the aq. layer was extracted with DCM (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by supercritical-fluid chromatography (Chiralcel OJ-H (250×21 mm, 5 μm), 55% liquid CO2/45% 1:1:1 MeOH:EtOH:IPA (+20 mM aq. NH4OH), 75 mL/min) separately provided 2-(2-((2-chlorophenyl)amino)-quinolin-8-yl)-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (107; 9.7 mg, 0.025 mmol, 14% yield; first-eluting compound) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.47 (1H, br. s.), 9.73 (1H, br. s.), 8.17 (2H, t, J=8.9 Hz), 8.06 (1H, d, J=9.0 Hz), 7.59 (2H, t, J=7.6 Hz), 7.39 (3H, quin, J=7.8 Hz), 7.22 (1H, t, J=7.6 Hz), 6.99 (2H, d, J=8.6 Hz), 6.94 (1H, s), 6.08 (1H, d, J=7.0 Hz). m/z (ESI, +ve) 387.0 (M+H)+: and 2-(2-((2-chlorophenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (108; 14.0 mg, 0.036 mmol, 20% yield; second-eluting compound) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.16 (1H, s), 8.04 (3H, t, J=8.7 Hz), 7.53 (2H, d, J=8.0 Hz), 7.35-7.41 (1H, m), 7.31 (2H, t, J=7.8 Hz), 7.09-7.18 (2H, m), 6.95 (1H, d, J=8.8 Hz), 5.32 (1H, br. s.), 3.53-3.60 (2H, m), 2.68 (2H, br. s.). m/z (ESI, +ve) 389.1 (M+H)+.

Aufarbeitung

  1. customThe mixture was then partitioned between DCM (50 mL) and saturated aq. NH4Cl (30 mL)
  2. customThe organic layer was separated
  3. extractionthe aq. layer was extracted with DCM (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aa8839ca87b64a4684d9e915f437d28b
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09394297B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion