ChemicalBook CAS DataBase List 7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline

7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline synthesis

6synthesis methods

Product Name:7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline
CAS Number:1083325-87-4
Molecular formula:C12H9BrN4
Molecular Weight:289.13

89891-65-6
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761446-44-0 Synthesis

1-Methyl-4-pyrazole boronic acid pinacol ester

761446-44-0
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7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline

1083325-87-4
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Yield:1083325-87-4 89%

Reaction Conditions:

with sodium carbonate;palladium diacetate;triphenylphosphine in 1,2-dimethoxyethane;water for 4 h;Product distribution / selectivity;Reflux;

Steps:

A.A1.b-1
Intermediate 1 (502g; 2.06mol), 1 -methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)-1 H-pyrazole (450.42g; 2.16mol), triphenylphosphine (10.82g; 0.041 mol) and palladium(ll)acetate were added to a mixture of sodium carbonate (240.37g; 2.267mol), 1 ,2-dimethoxyethane (5.48L) and water (1.13L). The reaction mixture was stirred at reflux for 20 hours, then 1 -methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H- pyrazole (42.9g; 0.206 mol) was added and the reaction mixture refluxed until complete conversion (4 hours). The reaction mixture was poured out in water, stirred for 2 hours at room temperature, filtered and the precipitate was washed with water. The precipitate was then triturated in methanol and filtered. The precipitate was washed with methanol and dried to give 532.2g (89%) of intermediate 2 (off-white powder).

References:

ASTEX THERAPEUTICS LIMITED;SAXTY, Gordon;MURRAY, Christopher William;BERDINI, Valerio;BESONG, Gilbert Ebai;HAMLETT, Christopher Charles Frederick;JOHNSON, Christopher Norbert;WOODHEAD, Steven John;READER, Michael;REES, David Charles;MEVELLEC, Laurence Anne;ANGIBAUD, Patrick René;FREYNE, Eddy Jean Edgard;GOVAERTS, Tom Cornelis Hortense;WEERTS, Johan Erwin Edmond;PERERA, Timothy Pietro Suren;GILISSEN, Ronaldus Arnodus Hendrika Joseph;WROBLOWSKI, Berthold;LACRAMPE, Jean Fernand Armand;PAPANIKOS, Alexandra;QUEROLLE, Oliver Alexis Georges;PASQUIER, Elisabeth Thérèse Jeanne;PILATTE, Isabelle Noëlle Constance;BONNET, Pascal Ghislain André;EMBRECHTS, Werner Constant Johan;AKKARI, Rhalid;MEERPOEL, Lieven WO2011/135376, 2011, A1 Location in patent:Page/Page column 182

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