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Nitrogen → 2-(2-Chloro-5-isopropenyl-pyridin-4-ylamino)-N-methyl-benzamide

HRID 62516
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 62516
N#N.Br[C:4]1[C:5]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([NH:16][CH3:17])=[O:15])=[CH:6][C:7]([Cl:10])=[N:8][CH:9]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:30]1(C)[CH:35]=CC=C[CH:31]=1>O.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>[Cl:10][C:7]1[CH:6]=[C:5]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([NH:16][CH3:17])=[O:15])[C:4]([C:30]([CH3:35])=[CH2:31])=[CH:9][N:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 575169042-[(5-Bromo-2-chloro-4-pyridinyl)amino]-N-methylbenzamide

Produkt 1

HCID 575169072-(2-Chloro-5-isopropenyl-pyridin-4-ylamino)-N-methyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In a tube a solution of isopropenyboronic acid pinacol ester (3.31 mL, 17.6 mmole, 3 eq) in toluene (200 mL) was degassed with N2 at 50° C. for 15 min. To this was added Pd(PPh3)4 (0.68 g, 0.59 mmole, 0.1 eq) and 2-(5-bromo-2-chloro-pyridin-4-ylamino)-N-methyl-benzamide (2 g, 5.87 mmole, 1 eq). This mixture was again degassed with N2 for 30 min. A degassed solution of K3PO4 (4.98 g, 23.48 mmole, 4 eq) in H2O (8 mL) was added to the above mixture in one portion and the resulting mixture was heated at 110° C. for overnight. After completion of the reaction, it was allowed to cool to room temperature and solvent was removed under reduced pressure to yield crude product. It was purified by column chromatography over silica gel (60-120 mesh) using 0.5% MeOH-DCM as the eluant to give the title compound as an off white solid (0.8 g, 45%). 1H-NMR (400 MHz, DMSO-d6): δ 2.06 (s, 3H), 2.73-2.74 (d, 3H, J=4.52 Hz), 5.14 (s, 1H), 5.46 (s, 1H), 7.04-7.15 (m, 2H), 7.45-7.60 (m, 2H), 7.64-7.71 (m, 1H), 7.96 (s, 1H), 8.60-8.72 (brs, 1H), 9.87 (s, 1H). LC-MS [M+H]+=302.2.

Aufarbeitung

  1. customThis mixture was again degassed with N2 for 30 min
  2. customAfter completion of the reaction, it
  3. temperatureto cool to room temperature
  4. customsolvent was removed under reduced pressure
  5. customto yield crude product
  6. customIt was purified by column chromatography over silica gel (60-120 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-69b4e772eb31435f9756ed06b045174c
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09446034B2

Notizen zur Reaktion

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