ChemicalBook CAS DataBase List 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide synthesis

8synthesis methods

Product Name:2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide
CAS Number:1083326-73-1
Molecular formula:C18H21BF2N2O5S
Molecular Weight:426.24

1086063-46-8 Synthesis

N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide

1086063-46-8
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2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

1083326-73-1
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$129.00/100mg

Yield: 100%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;potassium acetate in 1,4-dioxane at 90; for 7 h;Inert atmosphere;

Steps:

1.4 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide
To a suspension of N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide (16.90 g, 44.6 mmol) in 1,4-dioxane (300 mL) was added bis(pinacolato)diboron (13.59 g, 53.5 mmol), followed by the addition of Pd(dppf)Cl₂.CH₂Cl₂(3.67 g, 4.5 mmol) and potassium acetate (13.12 g, 133.8 mmol). The reaction mixture was degassed with N₂for 3 times, then heated to 90° C. and stirred further for 7 hours. The mixture was then cooled to rt, quenched with H₂O (100 mL) and extracted with EtOAc (500 mL×3). The combined organic phases were washed with brine (500 mL×3), dried over anhydrous Na₂SO₄, and concentrated in vacuo to give the title compound as a pale yellow solid (24.00 g, 100%). [0306] MS (ESI, pos. ion) m/z: 427.0 [M+H]⁺. [0307] ¹H NMR (400 MHz, CDCl₃) δ (ppm): 8.25 (d, J=1.0 Hz, 1H), 8.04 (s, 1H), 7.85 (m, 1H), 7.14 (s, 1H), 6.93 (m, 2H), 3.91 (s, 3H), 1.33 (s, 12H).

References:

SUNSHINE LAKE PHARMA CO., LTD.;CALITOR SCIENCES, LLC;Xi, Ning US2014/234254, 2014, A1 Location in patent:Paragraph 0305; 0306; 0307