3-FORMYL-5-ISOPROPOXYPHENYLBORONIC ACID synthesis

Yield:1001414-26-1 71%

Reaction Conditions:

with sodium hydrogencarbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in water;N,N-dimethyl-formamide at 120; for 0.25 h;Microwave on 50 watts;Suzuki Coupling;

Steps:

99

3-bromo-l-(phenylsulfonyl)-lH-pyrrolo[2,3-b]pyridine (750 mg, 0.0022 mol) and 3- formyl-5-isopropoxyphenylboronic acid (510 mg, O.0024 mol) were dissolved in N,N- Dimethylformamide (10 mL, 0.2 mol) and then added 1.2 M of Sodium bicarbonate in water (6 mL) and [l,r-Bis(diphenylphosphino)ferrocene]dichloropalladiuin(II),complex with dichlorornethane (1:1) (20 mg, 0.00002 mol). Flushed with nitrogen and The reaction was microwaved on 50 watts, 120⁰C for 15 minutes. LC-MS showed complete reaction (1.99min, ES+/421.07) Worked up with DCM and water. Dried over MgSO4. Purified on silica gel column with 0-100%EtOAc to give the desired product as a yellow syrup (665mg, 71%) MS (ES+) m/z 421.07 (M+l). IHNMR (CDC13, 400MHz): 10.03(s, IH), 8.50(d, IH), 8.26 (d, 2H), 8.13 (d, IH), 7.97 (s, IH), 7.66 (s, IH), 7.60 (t, IH), 7.51 (t, 2H), 7.38 (s, 2H)7.26 (dd, IH), 4.72 (qd, IH), 1.41 (d, 6H)

References:

WO2008/5457,2008,A2 Location in patent:Page/Page column 151-152