Sodium Acetate → HCID 50942140, Verbindung

HRID 2174887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174887
C([O-])(=O)C.[Na+].Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]([O:15]CC)=O.Cl.[NH2:19][C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=1B(O)O>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[O:15]=[C:13]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[C:21]2[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:20]=2[NH:19]1

Komponenten

6

Edukt 3

HCID 517045Sodium AcetateHCID 15141565Ethyl 3-bromoisonicotinateHCID 441187662-Amino-4-cyanobenzeneboronic acid hydrochloride

Produkt 1

HCID 50942140HCID 50942140, VerbindungAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Sodium acetate (410 mg, 5 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (complexed with dichloromethane) (36 mg, 0.05 mmol) were added to a mixture of ethyl 3-bromo-4-pyridine carboxylate (230 mg, 1.0 mmol) and 2-amino-4-cyanophenylboronic acid hydrochloric acid salt (179 mg, 0.9 mmol). The mixture was connected to an exit bubbler and heated to 120° C. for 18 hours at which time LCMS analysis indicated that the reaction was done based on the disappearance of starting material. After cooling to room temperature, water was added and the dark solids were filtered and washed with dichloromethane to give 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carbonitrile (156 mg) as a gray solid which was sufficiently pure enough for subsequent chemical transformations. LCMS (ESI) 222.4 (M+1)+. 1HNMR (400 MHz, DMSO-d6) 12.2 (1H, s), 9.96 (1H, s), 8.90 (1H, d, 5.1 Hz), 8.77 (1H, d, 8.2 Hz), 8.13 (1H, d, 5.1 Hz), 7.73 (1H, dd 8.2, 1.6 Hz), 7.70 (1H, d, 1.6 Hz).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe dark solids were filtered
  3. washwashed with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-f4978b4b53a643f1bd7077298a3ccfd2
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062043B2

Notizen zur Reaktion

Wird geladen…