Reaktion #90543

Reaktionsgleichung

143

5-bromo-6-methoxy-2-(4-((trifluoromethyl)thio)benzyl)-2,3-dihydro-1H-inden-1-one

1-methylpiperidin-4-amine

cesium carbonate

BINAP

→

crude compound 144

6-methoxy-5-((1-methylpiperidin-4-yl)amino)-2-(4-((trifluoromethyl)thio)benzyl)-2, 3-dihydro-1H-inden-1-one

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was degassed
2. 2
   Sonstigepurged with nitrogen for 10 min
3. 3
   Sonstigeagain degassed
4. 4
   Sonstigepurged with nitrogen for another 10 min
5. 5
   workup.ADDITIONThe reaction was diluted with chloroform
6. 6
   Filtrationfiltered through celite bed
7. 7
   EinengenThe organic layer was concentrated

Vorschrift

To a solution of 143 (75 mg, 0.174 mol) and 1-methylpiperidin-4-amine 134 (23.8 mg, 0.0208 mol) in toluene 15 mL was added cesium carbonate (113.3 mg, 0.348 mol). The reaction was degassed and purged with nitrogen for 10 min. Pd2(dba)3 (7.96 mg, 0.0087 mol) and BINAP (10.8 mg, 0.0174 mol) was added and again degassed and purged with nitrogen for another 10 min. The reaction was heated to 110° C. overnight under sealed conditions. The reaction was diluted with chloroform and filtered through celite bed. The organic layer was concentrated to get the crude compound 144 and was purified through flash chromatography by using 100-200 mesh silica gel eluting the compound at 7.5% methanol in chloroform as brown coloured solid 6-methoxy-5-((1-methylpiperidin-4-yl)amino)-2-(4-((trifluoromethyl)thio)benzyl)-2, 3-dihydro-1H-inden-1-one 144. 1HNMR (400 MHz, CDCl3) δ ppm 7.55 (bs, 2H), 7.28 (bs, 2H), 7.08 (s, 1H), 6.42 (s, 1H), 4.99 (s, 1H), 3.89 (s, 3H), 3.37 (m, 4H), 2.84 (m, 6H), 2.66 (m, 3H), 2.09 (m, 4H); MS (ESI) m/z 465.0 (M+H).

Quelle