반응 #608377

반응 방정식

4-(cyanomethylidene)piperidinium chloride

X-Phos

4-bromo-1,2-dimethoxybenzene

Cs2CO3

Isocyanate

→

title compound

[1-(3,4-Dimethoxyphenyl)piperidin-4-ylidene]acetonitrile

용매

t-BuOH

반응 조건

후처리

1. 1
   기타The reaction mixture was purged with argon for 5 minutes
2. 2
   기타the reaction flask was capped
3. 3
   온도The reaction was then cooled to ambient temperature
4. 4
   workup.ADDITIONdiluted with DMF
5. 5
   기타The mixture was then passed through a nylon syringe
6. 6
   여과filter (0.45 μm)
7. 7
   농축the filtrate was concentrated in vacuo

실험 절차

In a sealed tube, 4-(cyanomethylidene)piperidinium chloride (16 mg, 0.10 mmol), Pd2(dba)3 (14 mg, 0.015 mmol), X-Phos (20 mg, 0.020 mmol), 4-bromo-1,2-dimethoxybenzene (33 mg, 0.15 mmol), and Cs2CO3 (98 mg, 0.30 mmol) were suspended in t-BuOH (0.5 mL). The reaction mixture was purged with argon for 5 minutes, the reaction flask was capped, and heated to 90° C. for 12 hours. The reaction was then cooled to ambient temperature and diluted with DMF:MeCN (1.0 mL, 50:50). To this mixture, Silica Supported-DMT (0.50 mmol, 0.57 mmol/g) followed by Silica Supported-Isocyanate (0.15 mmol, 1.33 mmol/g) was added. The resulting mixture was then shaken at 50° C. for 4 hours. The mixture was then passed through a nylon syringe filter (0.45 μm), and the filtrate was concentrated in vacuo to afford the title compound. The crude residue was used without further purification.

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