Reaktion #1705672

Reaktionsgleichung

6-bromo-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran]

4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

sodium hydride

→

6-Bromo-1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran]

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePrepared
2. 2
   SonstigeAfter purification 6-bromo-1-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]
3. 3
   Sonstigewas obtained as a yellow film

Vorschrift

Prepared according to procedure M using 6-bromo-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran] (98 mg, 367 μmol), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (100 mg, 367 μmol) in DMF (4.5 mL) and sodium hydride (18 mg, 0.73 mmol) and heating the reaction mixture at 130° C. for 8 h. After purification 6-bromo-1-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, d, J=5.1 Hz), 7.89-7.98 (2H, m), 7.85 (1H, dd, J=10.0, 2.5 Hz), 7.75 (1H, dd, J=9.2, 6.1 Hz), 7.41 (1H, ddd, J=6.7, 4.5, 2.5 Hz), 7.28-7.33 (1H, m), 7.07 (1H, d, J=7.8 Hz), 6.89 (1H, dd, J=7.8, 2.0 Hz), 6.11 (1H, d, J=2.0 Hz), 3.93-4.10 (4H, m), 3.45-3.60 (2H, m), 2.38 (3H, s), 2.08-2.25 (2H, m), 1.91 (1H, dd, J=13.9, 2.5 Hz), 1.81 (1H, dd, J=13.7, 2.3 Hz). Mass Spectrum (ESI) m/e 504 [(M+1) (79Br)] and 506 [(M+1) (81Br)].

Quelle