反応 #90539

反応方程式

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

溶媒

toluene

tBuOH

反応条件

後処理

1. 1
   その他The reaction was degassed
2. 2
   その他purged with nitrogen for 10 min
3. 3
   その他again degassed
4. 4
   その他purged with nitrogen for another 10 min
5. 5
   その他under sealed condition
6. 6
   workup.ADDITIONThe reaction was diluted with chloroform
7. 7
   ろ過filtered through celite bed
8. 8
   濃縮The organic layer was concentrated

実験手順

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.

出典