Cesium carbonate → Ethyl 6-(6-(3-ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2243023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2243023
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][N:8]=1)=[O:5])[CH3:2].I[C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[C:27]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]2=[O:42].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[N:8]=[CH:9][C:10]([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]([CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[C:27]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]3=[O:42])=[CH:11][CH:12]=1)[CH3:2]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 592084346-(3-Ethylureido)pyridine-3-boronic acid pinacol ester2×HCID 59208478Ethyl 6-iodo-1-[2-(methyloxy)ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Produkt 1

HCID 59208515Ethyl 6-(6-(3-ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 57646695Palladium;tetraphenyl-lambda5-phosphaneKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of N-ethyl-N′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)urea (Intermediate 1, 80 mg, 0.27 mmol), ethyl 6-iodo-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (WO2006010733, 100 mg, 0.25 mmol), cesium carbonate (90 mg, 0.27 mmol), and Tetrakisphenylphosphine palladium (28.9 mg, 0.02 mmol) in dioxane (4 mL) and water (1 mL) was degassed with nitrogen for 30 minutes. The reaction mixture was then heated in a microwave for 1 h at 110° C. The reaction mixture was cooled to room temperature and filtered, then placed on high vacuum to remove residual solvent (59 mg). MS (ESP): 439 (M+H+) for C23H26N4O5; NMR: 9.34 (s, 1H), 8.61 (m, 2H), 8.45 (m, 1H), 8.10 (m, 1H), 8.09 (m, 2H), 7.54 (m, 1H), 4.62 (m, 2H), 4.25 (m, 2H), 3.71 (m, 2H), 3.57 (s, 3H), 3.21 (m, 2H), 1.30 (t, J=7 Hz, 3H), 1.11 (t, J=8 Hz, 3H).

Aufarbeitung

  1. customwas degassed with nitrogen for 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove residual solvent (59 mg)

Quellen und Nachweise

ORD-Eintrag
ord-0b121e4ab7dd415d82270f905ac0474e
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674801B2

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