反应 #1256710

反应方程式

triflate

trifluoromethanesulfonic acid 4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl ester

Cs2CO3

benzophenone imine

→

title compound

收率 97.7%

4-(3,5-dimethylpyridin-4-yl)-N-(diphenylmethylene)-3,5-dimethyl-benzenamine

收率 97.7%

溶剂

THF

反应条件

后处理

1. 1
   其他The tube was evacuated
2. 2
   其他The Schlenk tube was sealed
3. 3
   其他the mixture was degassed by three freeze-thaw cycles
4. 4
   workup.STIRRINGThe mixture was then stirred at 65° C. for 15 h
5. 5
   workup.ADDITIONdiluted with methylene chloride (40 mL)
6. 6
   过滤filtered
7. 7
   浓缩the filtrate was concentrated in vacuo
8. 8
   其他The resulting yellow solid was purified by flash chromatography on silica gel
9. 9
   洗涤eluting with 1:1 hexane

实验过程

A flame-dried sealable Schlenk tube was charged with triflate 8 (0.359 g, 1.00 mmol), Cs2CO3 (0.456 g, 1.40 mmol), Pd(OAc)2 (6.7 mg, 0.030 mmol), and BINAP (28.2 mg, 0.0450 mmol). The tube was evacuated and then backfilled with N2. Next, a solution of benzophenone imine (0.224 g, 1.20 mmol) in dry THF (4 mL) was added with stirring under an N2 flow. The Schlenk tube was sealed, the mixture was degassed by three freeze-thaw cycles, and backfilled with N2. The mixture was then stirred at 65° C. for 15 h. The reaction mixture was next cooled to room temperature, diluted with methylene chloride (40 mL), filtered, and the filtrate was concentrated in vacuo. The resulting yellow solid was purified by flash chromatography on silica gel, eluting with 1:1 hexane: ethyl acetate, to give 0.381 g (97.7%) of the title compound as a colorless solid: mp 44-45° C.; 1H NMR (400 MHz, CD2Cl2): δ 8.305 (s, 2H), 7.774 (d, 2H, J=8.0 Hz), 7.494-7.408 (m, 3H), 7.271 (m, 3H), 7.144 (d, 2H, J=6.8 Hz), 6.476 (s, 2H), 1.828 (s, 6H), 1.706 (s, 6H); 13C NMR (100 MHz, CD2Cl2): δ 168.647, 151.523, 148.783, 148.611, 140.013, 136.737, 135.099, 132.206, 131.678, 131.114, 130.040, 129.685, 128.912, 128.583, 128.038, 120.459, 19.842, 16.594; MS(ESI): m/z 391.5 [(M+H)+, 100]; Anal. Calcd. for C28H26N2: C, 86.12; H, 6.71; N, 7.17. Found; C, 85.86; H, 6.74; N, 7.17.

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