Sodium Carbonate → Ethanesulfonic acid [5-(8-fluoro-1-methyl-2-oxo-1,2-dihydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774889
[F:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2.Br[C:24]1[CH:25]=[C:26]([CH2:30][NH:31][S:32]([CH2:35][CH3:36])(=[O:34])=[O:33])[CH:27]=[N:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:25]=[C:26]([CH2:30][NH:31][S:32]([CH2:35][CH3:36])(=[O:33])=[O:34])[CH:27]=[N:28][CH:29]=2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH:8]=[CH:7]2

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 58215658HCID 58215658, VerbindungHCID 726988268-Fluoro-1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 86679239Ethanesulfonic acid [5-(8-fluoro-1-methyl-2-oxo-1,2-dihydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amideAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 8-fluoro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (example 208 [E], 20 mg, 0.066 mmol), ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (intermediate A-11, 27.4 mg, 0.098 mmol), bis(triphenylphosphine)-palladium(II) chloride (4.6 mg, 0.0066 mmol), and aq. sodium carbonate solution (2 N, 0.07 mL) in DMF (1 mL) was heated in a microwave at 120° C. for 30 minutes. After dilution of the reaction mixture with EtOAc, the organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was then purified by prep-HPLC to afford the title compound (2.5 mg, 10%) as a white solid. MS: 376.3 (M+H+)+.

Aufarbeitung

  1. washAfter dilution of the reaction mixture with EtOAc, the organic layer was washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was then purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-555770becf1f4df7afc2c1e5a7b41b31
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260408B2

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