4-METHYL-2-(TRIBUTYLSTANNYL)THIAZOLE synthesis
- Product Name:4-METHYL-2-(TRIBUTYLSTANNYL)THIAZOLE
- CAS Number:251635-59-3
- Molecular formula:C16H31NSSn
- Molecular Weight:388.2
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Yield:-
Reaction Conditions:
Stage #1:2-bromo-4-(trifluoromethyl)thiazole with n-butyllithium in tetrahydrofuran;hexane at -78; for 0.5 h;Inert atmosphere;
Stage #2:tributyltin chloride in tetrahydrofuran;hexane at -78; for 16 h;
Steps:
77.1
To a solution of 2-bromo-4-(trifluoromethyl)thiazole in tetrahydrofuran (10 mL) at -78 °C under N2 atmosphere was added n-Butyl lithium (2.5 M in hexane) and the reaction mixture was stirred at same temperature. After 30 mm, tributyltin chloride was added to the reaction mixture at -78 °C and stirred at ft. After 16 h, the reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate (2*25 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated to afford 2-(tributylstannyl)-4-(Rs)-thiazole [219A to Ci as a yellow liquid. LCMS inconclusive and it was taken as such for next step.
References:
CADENT THERAPEUTICS, INC.;ERIKSEN, Birgitte, Langer;GUSTAFSSON, Magnus;HOUGAARD, Charlotte;JACOBSEN, Thomas, Amos;JEFSON, Martin, R.;KLEIN, Jessica;LARSEN, Janus, Schreiber;LOWE, John, A., III;MCCALL, John, M.;STROØBÆK, Dorte;VON SCHOUBYE, Nadia, Lybøl;KEANEY, Gregg, F. WO2017/210545, 2017, A1 Location in patent:Paragraph 00289; 00290
