Phosphonic acid, P-[(6-Methyl-2-pyridinyl)(phenylaMino)Methyl]-, diphenyl ester synthesis

4synthesis methods

Product Name:Phosphonic acid, P-[(6-Methyl-2-pyridinyl)(phenylaMino)Methyl]-, diphenyl ester
CAS Number:614750-85-5
Molecular formula:C25H23N2O3P
Molecular Weight:430.44

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62-53-3 Synthesis

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Phosphonic acid, P-[(6-Methyl-2-pyridinyl)(phenylaMino)Methyl]-, diphenyl ester

614750-85-5
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Yield:614750-85-5 100%

Reaction Conditions:

with zirconyl chloride octahydrate in isopropyl alcohol at 20; for 2 h;

Steps:

A Step A: diphenyl (6-methylpyridin-2-yl)(phenylamino)methylphosphonate

A mixture of 6-methylpicolinaldehyde (1.00 g, 8.26 mmol), diphenyl phosphite (1.92 mL, 9.91 mmol), aniline (754 μL, 8.26 mmol) and ZrOCl₂8H₂O (266 mg, 0.826 mmol) in i-PrOH (16 mL) was stirred at room temperature for 2 hours. The reaction mixture was quenched with water and then extracted with DCM twice. The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO₂(Hexanes:EtOAc=7:3 to 3:2) to afford diphenyl (6-methylpyridin-2-yl)(phenylamino)methylphosphonate (3.67 g, quant.) as a yellow solid. ¹H-NMR (400 MHz, CDCl₃): δ 7.51 (1H, t, J=7.6 Hz), 7.35 (1H, d, J=7.6 Hz), 7.25-7.23 (4H, m), 7.21-7.10 (4H, m), 7.08-7.00 (4H, m), 6.78-6.73 (3H, m), 5.48 (1H, t, J=7.6 Hz), 5.32 (1H, dd, J=21.0, 8.0 Hz), 2.52 (3H, s).

References:

US2020/231591,2020,A1 Location in patent:Paragraph 0098; 0119; 0120

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