ChemicalBook CAS DataBase List Benzoic acid, 5-broMo-3-[ethyl(tetrahydro-2H-pyran-4-yl)aMino]-2-Methyl-, Methyl ester

Benzoic acid, 5-broMo-3-[ethyl(tetrahydro-2H-pyran-4-yl)aMino]-2-Methyl-, Methyl ester synthesis

10synthesis methods

Product Name:Benzoic acid, 5-broMo-3-[ethyl(tetrahydro-2H-pyran-4-yl)aMino]-2-Methyl-, Methyl ester
CAS Number:1403257-79-3
Molecular formula:C16H22BrNO3
Molecular Weight:356.25

Benzoic acid, 5-broMo-2-Methyl-3-[(tetrahydro-2H-pyran-4-yl)aMino]-, Methyl ester

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75-07-0 Synthesis

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Benzoic acid, 5-broMo-3-[ethyl(tetrahydro-2H-pyran-4-yl)aMino]-2-Methyl-, Methyl ester

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Yield: 100%

Reaction Conditions:

with sodium tris(acetoxy)borohydride;acetic acid in dichloromethane at 20; for 24 h;

Steps:

Methyl 5-bromo-3-[ethyl(oxan-4-yl)amino]-2-methylbenzoate
To a stirred solution of methyl 5-bromo-2-methyl-3-[(oxan-4-yl)amino]benzoate (39.1 g, 119 mmol) in CH₂Cl₂ (400 mL) and AcOH (40 mL) was added acetaldehyde (24.7 g, 476 mmol) and sodium triacetoxyborohydride (79.6 g, 357 mmol). The reaction mixture was stirred at RT for 24 hours. Then saturated NaHCO₃ aq.was added and the mixture was separated. The aqueous layer was extracted with CH₂Cl₂ and the combined organic layer was concentrated in vacuo. The residue was purified by silica gel column chromatography (SiO₂Heptane/EtOAc=3/1) to give the titled compound as a viscous oil (44.1 g, quantitative yield). ¹H-NMR (400 MHz, DMSO-d₆) δ ppm; 7.62 (s, 1H), 7.52 (s, 1H), 3.80 (m, 5H), 3.31 (m, 2H), 2.97-3.05 (m, 2H), 2.87-2.96 (m, 1H), 2.38 (s, 3H), 1.52-1.61 (m, 2H), 1.37-1.50 (m, 2H), 0.87 (t, J=6.8 Hz, 3H).

References:

Kuntz, Kevin Wayne;Campbell, John Emmerson;Seki, Masashi US2014/107122, 2014, A1 Location in patent:Paragraph 0191; 0192

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