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To a solution of 5-bromo-1-methyl-1 ,3-diotahydro-indol-2-one (CASNo. 20870-90-0, 4.07 g, 18.00 mmol). in DMSO (50 mL) was added biotas(pinaco.ato)diboron (5 03 g, 19.80 mmol), and potassium acetate (5.30 g, 54 0 mmol) Next, [1 , 1 ‘-biotas(diphenylphosphiotano)- ferrocene]-d(chloropalladiotaum(ll) complexed with dichloromethane (CASNo. 72287-26-4, 0 417 g, 0 540 mmol) was added The reaction mixture was degassed by bubbling nitrogen through the solution for 3 minutes The reaction was then heated at 80 C for 18 hr The reaction was then poured into ice-water and extracted three times with diethyl ether, The organic extracts were combined, washed with brine, dned over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, O to 70%) to afford 1-methyl-5-(4,4,5,5- tetramethyl-(1 ,3,2Jdioxaboro.an-2-yl)-1 ,3-diotahydro-indol-2-one, 1H NMR (400 MHz1 CDCI3) delta ppm 1 35 (s, 12 H), 3.23 (s, 3 H), 3.51 (s, 2 H), 6 83 (d, J=7,6 Hz, 1 H), 7.69 (S1 1 H)1 7,77 (d, J= 7 8 Hz, 1 H),
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Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
Indoline – Wikipedia,
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