Reaktion #680468

Reaktionsgleichung

Intermediate A2

2-Chloro-4-(4-fluoro-2-methoxyphenyl)pyridine

(3-aminophenyl)methanesulfonamide

NaOC(CH3)3

(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)

→

[3-((4-(4-Fluoro-2-methoxyphenyl)pyridin-2-yl)amino)phenyl]-methanesulfonamide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged for 10 minutes with nitrogen
2. 2
   Filtrationwas filtered
3. 3
   Waschenthe residue washed with toluene
4. 4
   EinengenThe filtrate was concentrated under reduced pressure
5. 5
   Sonstigepurified by automated column chromatography (ISCO, gradient MeOH/DCM)
6. 6
   Sonstigewere further purified by preparative HPLC
7. 7
   Sonstigeto yield 24 mg (12%) of G1 as an off-white solid

Vorschrift

Intermediate A2 (119 mg, 0.5 mmol), (3-aminophenyl)methanesulfonamide (112 mg, 0.6 mmol), NaOC(CH3)3 (67 mg, 0.7 mmol), PdCl2(CH3CN)2 (6.5 mg, 0.025 mmol, 5 mol %), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) [Xantphos] (23 mg, 0.04 mmol, 8 mol %) were dissolved in dry DMF (4 mL) and purged for 10 minutes with nitrogen. After heating at 110° C. for 18 hours the reaction mixture was filtered and the residue washed with toluene. The filtrate was concentrated under reduced pressure and purified by automated column chromatography (ISCO, gradient MeOH/DCM). The collected fractions which contained the title compound were further purified by preparative HPLC to yield 24 mg (12%) of G1 as an off-white solid. 1H NMR (300 MHz, d6-DMSO, 298K) δ 3.84 (s, 3H), 4.22 (s, 2H), 6.81-6.94 (m, 5H), 6.98 (s, 1H), 7.07 (dd, J=11.7 Hz, J=4.2 Hz, 1H), 7.26 (t, J=6.6 Hz, 1H), 7.39 (dd, J=6.9 Hz, J=6.0 Hz, 1H), 7.56-7.61 (m, 1H), 7.79 (d, J=7.5 Hz, 1H), 8.16 (d, J=6.0 Hz, 1H), 9.12 (s, 1H).

Quelle