반응 #58494

반응 방정식

2-bromo-6-(1-t-butoxycarbonylpiperidin-4-ylcarbonyl)-pyridine

N-methyl-2,4,6-trifluorobenzamide

BINAP

sodium t-butoxide

N-methyl-2,4,6-trifluorobenzamide

BINAP

sodium t-butoxide

→

2,4,6-trifluoro-N-methyl-N-[6-(1-t-butoxycarbonyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide

수율 44.0%

용매

toluene

반응 조건

후처리

1. 1
   온도Heat
2. 2
   온도Cool
3. 3
   기타the reaction to room temperature
4. 4
   기타Re-heat the reaction at 85° C. for 16 more hours
5. 5
   추출Extract the reaction mixture with ethyl acetate and aqueous NaOH (0.1 N)
6. 6
   기타Collect
7. 7
   기타dry the organic layers
8. 8
   농축Concentrate
9. 9
   기타purify the crude product by chromatography (silica gel, 10% -30% ethyl acetate/hexane)

실험 절차

Heat a mixture of 2-bromo-6-(1-t-butoxycarbonylpiperidin-4-ylcarbonyl)-pyridine (152 mg, 0.41 mmol), N-methyl-2,4,6-trifluorobenzamide (92.6 mg, 0.49 mmol), Pd2(dba)3 (9.2 mg, 0.01 mmol), BINAP (12.4 mg, 0.02 mmol), sodium t-butoxide (55 mg, 0.57 mmol) in anhydrous toluene (10 mL) at 85° C. for 16 hrs. Cool the reaction to room temperature and add another aliquot of N-methyl-2,4,6-trifluorobenzamide, Pd2(dba)3, BINAP and sodium t-butoxide in the same amount. Re-heat the reaction at 85° C. for 16 more hours. Extract the reaction mixture with ethyl acetate and aqueous NaOH (0.1 N). Collect and dry the organic layers. Concentrate and purify the crude product by chromatography (silica gel, 10% -30% ethyl acetate/hexane) to obtain 2,4,6-trifluoro-N-methyl-N-[6-(1-t-butoxycarbonyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide (86 mg, 44% yield).

출처