反応 #1256710

反応方程式

triflate

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

Cs2CO3

benzophenone imine

→

title compound

収率 97.7%

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

収率 97.7%

溶媒

THF

反応条件

後処理

1. 1
   その他The tube was evacuated
2. 2
   その他The Schlenk tube was sealed
3. 3
   その他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
   ろ過filtered
7. 7
   濃縮the filtrate was concentrated in vacuo
8. 8
   その他The resulting yellow solid was purified by flash chromatography on silica gel
9. 9
   洗浄eluting with 1:1 hexane

実験手順

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.

出典