Réaction #90539

Équation de réaction

104

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

4-methylpiperidine

cesium carbonate

BINAP

→

crude compound 139

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

Solvants

toluene

tBuOH

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
   Autreunder sealed condition
6. 6
   workup.ADDITIONThe reaction was diluted with chloroform
7. 7
   Filtrationfiltered through celite bed
8. 8
   ConcentrationThe organic layer was concentrated

Mode opératoire

To a solution of 104 (150 mg, 0.348 mmol) and 4-methylpiperidine (69 mg, 0.696 mmol) in toluene and tBuOH (8:2, 10 mL) was added cesium carbonate 228 mg, 0.696). The reaction was degassed and purged with nitrogen for 10 min. Pd2(dba)3 (15.9 mg, 0.0174 mmol) and BINAP (32.4 mg, 0.15 m·mol) was added and again degassed and purged with nitrogen for another 10 min. The reaction was heated to 110° C. for overnight under sealed condition. The reaction was diluted with chloroform and filtered through celite bed. The organic layer was concentrated to get the crude compound 139 which was purified through flash chromatography by using 100-200 mesh silica gel eluting the compound at 10% ethyl acetate in hexane as pale yellow coloured solid (E)-6-methoxy-5-(4-methylpiperidin-1-yl)-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one 139.

Source