Sodium Carbonate → 5-Benzo[1,3]dioxol-5-yl-3-furan-3-yl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

Bromide 14 (17.6 mg, 0.07 mmol), 3,4-(methylenedioxy)phenylboronic acid (16.7 mg, 0.10 mmol), LiCl (8.4 mg, 0.20 mmol), PdCl2(Ph3P)2 (4.6 mg, 0.007 mmol) in 1 M aqueous Na2CO3 (0.17 mL, 0.17 mmol), PhMe (1.5 mL) and EtOH (1.5 mL) was heated at 105° C. After 5 h the mixture was allowed to cool to r.t. and then purified by PTLC with AcOEt:hexane=1:1 as eluent to afford azaindole 15 (15.2 mg, 76%) as a white solid. 1H NMR (400 MHz; CDCl3) δ 6.04 (s, 2H), 6.72 (dd, J=0.8 and 1.8 Hz, 1H), 6.94 (dd, J=7.9, 0.3 Hz, 1H), 7.08-7.12 (m, 2H), 7.48 (d, J=2.3 Hz, 1H), 7.54 (t, J=1.6 Hz, 1H), 7.82 (t, J=1.1 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 8.52 (d, J=2.1 Hz, 1H), 9.61 (brs, NH).

Provenance & Evidence