4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-QUINOLINE synthesis
- Product Name:4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-QUINOLINE
- CAS Number:1035458-54-8
- Molecular formula:C15H18BNO2
- Molecular Weight:255.12
73183-34-3
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3964-04-3
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1035458-54-8
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Yield:-
Reaction Conditions:
with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane at 20 - 100; for 2 h;Inert atmosphere;
Steps:
462.A; 463.A Step A: 4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)quinoline
To a stirred solution of 4-bromoquinoline (2.00 g, 9.61 mmol) in 1,4-dioxane (15 mL) were added 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (3.66 g, 14.42 mmol), acetylpotassium (2.37 g, 28.80 mmol) and Pd(dppf)C12 (1.41 g, 1.92 mmol) under nitrogen at ambient temperature. After the resulting mixture was stirred at 100°C for 2hr, it was diluted with water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (3 x 100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel chromatography, eluting with 10%-50%EA in PE to afford crude of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolineas a solid (purity 60%). LCMS (ESI) calc’d forC15H18BNO2:[M + 1]256 found 256;’H NMR (300 MHz, DMSO-d6)ö 8.97 (d, J= 4.2 Hz, 1H), 8.59 (d, J= 8.4 Hz, 1H), 8.07 (d, J= 8.1 Hz, 1H), 7.88-7.83 (m, 2H), 7.71 (t, J= 7.2 Hz, 1H), 1.40 (s, 12H).
References:
MERCK SHARP & DOHME CORP.;BENNETT, Frank;JIANG, Jinlong;PASTERNAK, Alexander;DONG, Shuzhi;GU, Xin;SCOTT, Jack D.;TANG, Haiqun;ZHAO, Zhiqiang;HUANG, Yuhua;HUNTER, David;YANG, Dexi;ZHANG, Zhibo;FU, Jianmin;BAI, Yunfeng;ZHENG, Zhixiang;ZHANG, Xu;YOUNG, Katherine;XIAO, Li WO2016/206101, 2016, A1 Location in patent:Page/Page column 380; 381
611-35-8
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73183-34-3
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91-22-5
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1035458-54-8
92 suppliers
$18.00/100mg