Sodium Carbonate → 5-[2-(4-Trifluoromethyl-phenyl)-vinyl]1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of bromide 27 (76 mg, 0.39 mmol), lithium chloride (49 mg, 1.16 mmol), trans-2[4-(trifluoromethyl)-phenyl]vinyl boronic acid (125 mg, 0.58 mmol) in a mixture of toluene (3 mL), EtOH (3 mL) and 1 M aqueous Na2CO3 solution (0.96 mL, 0.96 mmol) was added (PPh3)2PdCl2 (27 mg, 0.04 mmol) in one portion. The mixture was heated in the dark to 105° C. under a nitrogen atmosphere for 20 h, filtered through a pad of cotton wool and concentrated. The residue was purified by PTLC with CH2Cl2:MeOH=98:2 as eluent to afford styrene 28 (51 mg, 46%) as a pale yellow solid. 1H NMR (400 MHz; CDCl3) δ 6.55 (dd, J=2.0, 3.5 Hz, 1H), 7.15 (d, J=16.3 Hz, 1H), 7.31 (d, J=16.3 Hz, 1H), 7.35 (m, 1H), 7.62 (s, 4H), 8.13 (d, J=1.8 Hz, 1H), 8.50 (m, 1H), 9.17 (br s, NH).

Provenance & Evidence