반응 #821720

반응 방정식

N-Boc-piperazine

2-methyl-5-quinolinyl trifluoromethanesulfonate

cesium carbonate

(+/−)-bis(diphenylphosphino)-1,1′-binaphthyl

→

title compound

1,1-Dimethylethyl 4-(2-methyl-5-quinolinyl)-1-piperazinecarboxylate

용매

toluene

반응 조건

후처리

1. 1
   기타then flushed with nitrogen
2. 2
   온도The solution was cooled
3. 3
   농축concentrated
4. 4
   workup.ADDITIONwere added
5. 5
   기타giving a suspension
6. 6
   workup.STIRRINGThe suspension was stirred for 30 minutes
7. 7
   여과filtered over a pad of Silica Gel (approx 2.5 vol)
8. 8
   세척The filtrate was washed with 10 vol of water
9. 9
   농축concentrated under reduced pressure

실험 절차

A solution of 2-methyl-5-quinolinyl trifluoromethanesulfonate (1 wt, 1 eq) in toluene (7 vol) was degassed under reduced pressure then flushed with nitrogen. To the mixture were added N-Boc-piperazine (1.05 eq), milled cesium carbonate (1.5 eq), (+/−)-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 0.15 eq) and palladium acetate (0.05 eq). The resulting mixture was stirred at 95° C. for 16 hours. The solution was cooled and concentrated to approx. 4 vol and 10 vol of cyclohexane were added giving a suspension. The suspension was stirred for 30 minutes and filtered over a pad of Silica Gel (approx 2.5 vol). The filtrate was washed with 10 vol of water and concentrated under reduced pressure to give the title compound as a brown solid, which was carried through directly to the next stage.

출처