Réaction #90545

Équation de réaction

152

(E)-5-bromo-6-methoxy-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one

4-methylpiperidine

cesium carbonate

BINAP

→

crude compound 153

(E)-6-methoxy-5-(4-methylpiperidin-1-yl)-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was degassed
2. 2
   Autrepurged with nitrogen for 10 min
3. 3
   Autreagain degassed
4. 4
   Autrepurged with nitrogen for another 10 min
5. 5
   workup.ADDITIONThe reaction was diluted with chloroform
6. 6
   Filtrationfiltered through celite bed
7. 7
   ConcentrationThe organic layer was concentrated

Mode opératoire

To a solution of 152 (120 mg, 0.3007 mmol) and 4-methylpiperidine 129 (60.2 mg, 0.6015 mmol) in toluene was added cesium carbonate (197.2 mg, 0.6015 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd2(dba)3 (13.7 mg, 0.0150 mmol) and BINAP (28.1 mg, 0.0451 mmol) 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 153 which was purified through flash chromatography by using 100-200 mesh silica gel eluting the compound (E)-6-methoxy-5-(4-methylpiperidin-1-yl)-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one 153 at 25% ethyl acetate in hexane as pale yellow coloured solid.

Source