ChemicalBook CAS DataBase List methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indene-1-carboxylate

methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indene-1-carboxylate synthesis

5synthesis methods

Product Name:methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indene-1-carboxylate
CAS Number:1423700-47-3
Molecular formula:C17H23BO4
Molecular Weight:302.17

(rac)-5-bromoindan-1-carboxylic acid methyl ester

112933-48-9
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73183-34-3
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methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indene-1-carboxylate

1423700-47-3
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Yield:1423700-47-3 60%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;sodium carbonate in 1,4-dioxane at 90; for 12 h;Inert atmosphere;

Steps:

X

To a stirred mixture of compound XI-5 (700 mg, 2.77 mmol), bis(pinacolato)diboron (1.05 g, 4.15 mmol) and Na₂C03 (587 mg, 5.54 mmol) in 1,4-dioxane (10 mL) was added Pd(dppf)Cl₂ (70 mg) under N₂ protection, and the mixture was stirred at 90 °C for 12 hrs. The mixture was diluted with EA (100 mL). The organic layer was separated, washed with water and brine, dried over Na₂S0₄ and concentrated. The residue was purified by column chromatography on silica gel (PE:EA=70:1) to give product XI-6 (500 mg, yield 60%). 1H NMR (CDCI₃, 400MHz) δ 7.71 (s, 1H), 7.64 (d, J=7.6 Hz, 1H), 7.38 (d, J=7.6 Hz, 1H), 4.07 (t, J=7.2 Hz, 1H), 2.87-3.13 (m, 2H), 2.28-2.48 (m, 2H), 1.34 (s, 12H).

References:

WO2013/25733,2013,A1 Location in patent:Paragraph 0467

34598-49-7 Synthesis