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