Reaktion #268

Reaktionsgleichung

CONC(=O)c1ccccc1Nc1c

Cc1cc(N)n(C(C)C)n1

→

CONC(=O)c1ccccc1Nc1c

Ausbeute 36.5%

Lösungsmittel

C1COCCO1

Reaktionsbedingungen

Vorschrift

2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and sodium 2-methylpropan-2-olate (92 mg, 0.96 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (74.1 mg, 0.13 mmol) and BIS(DIBENZYLIDENEACETONE)PALLADIUM(0) (55.3 mg, 0.10 mmol) were added and tube was sealed. Mixture was stirred at reflux overnight. Reaction was allowed to cool to room temperature, filtered, washed with CH2Cl2/MeOH (9/1, 10 mL) and concentrated to dryness. The crude product was purified by flash chromatography (dry loading) on silica gel eluting with 1 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford 2-(5-chloro-2-(1-isopropyl-3-methyl-1H-pyrazol-5-ylamino)pyridin-4-ylamino)-N-methoxybenzamide (97 mg, 36.5 %) as a pink foam.

Quelle