Sodium Carbonate → 7-Fluoro-8-methyl-2-(5-methylpyridin-3-yl)quinoline-3-carbaldehyde

HRID 572132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572132
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[N:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:14][C:6]1[C:5]([CH3:15])=[C:4]2[C:9]([CH:10]=[C:11]([CH:12]=[O:13])[C:2]([C:19]3[CH:20]=[N:21][CH:22]=[C:17]([CH3:16])[CH:18]=3)=[N:3]2)=[CH:8][CH:7]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27627085-Methylpyridine-3-boronic acidHCID 866626352-Chloro-7-fluoro-8-methylquinoline-3-carbaldehyde

Produkt 1

HCID 867011737-Fluoro-8-methyl-2-(5-methylpyridin-3-yl)quinoline-3-carbaldehydeAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Prepared according to the procedure described for Intermediate 41, utilising 2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde (5.0 g, 22.36 mmol), 5-methylpyridin-3-ylboronic acid (6.95 g, 50.75 mmol), tetrakis(triphenylphosphine)palladium(0) (258 mg, 0.22 mmol) and Na2CO3 (3.55 g, 33.54 mmol) in water (30 mL) and DME (60 mL). The crude material was triturated in diethyl ether (75 mL), and the solid was filtered off and dried under vacuum to give the title compound (5.0 g, 80%) as a brown solid. δH (DMSO-d6) 10.12 (s, 1H), 9.06 (s, 1H), 8.72 (d, J 1.9 Hz, 1H), 8.60 (d, J 1.5 Hz, 1H), 8.24 (dd, J 9.0, 6.4 Hz, 1H), 7.99 (d, J 0.6 Hz, 1H), 7.68 (t, J 9.2 Hz, 1H), 2.66 (d, J 2.4 Hz, 3H), 2.44 (s, 3H). LCMS (ES+) 281 (M+H)+, RT 1.66 minutes.

Aufarbeitung

  1. customPrepared
  2. customThe crude material was triturated in diethyl ether (75 mL)
  3. filtrationthe solid was filtered off
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6a2f2307d890428f838b821384acbc70
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029392B2

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