7-BROMO-1H-PYRROLO[2,3-C]PYRIDINE

Synthesis

19755-53-4

1826-67-1

165669-35-2

Example 1: Synthesis of [1-(4-methoxy-benzenesulfonyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-phenyl-amine (Compound 1); 7-bromo-6-azaindole (2 in Scheme 1): 2-bromo-3-nitropyridine (1 in Schemes 1,2, 2.0 g, 98%, 9.7 mmol) was dissolved in anhydrous THF (80 mL) and cooled the solution to -78 °C. An excess of vinyl magnesium bromide (1.0 M solution of THF, 40 mL, 40 mmol) was slowly added under nitrogen protection. The reaction mixture was stirred at -40 to -50 °C for 1 h. The reaction was subsequently quenched with saturated NaHCO3 solution. The organic and aqueous layers were separated and the aqueous layer was extracted with EtOAc (3 times). The organic layers were combined, dried with anhydrous MgSO4, filtered and the filtrate concentrated. The residue was purified by fast chromatography (eluent: EtOAc/hexane=1:2) to afford the target product 2 (1.1 g, 60%).1H NMR (500 MHz, CDCl3): δ 6.66 (dd, 1H, J=2.9,2.1Hz), 7.43 (dd, 1H, J=2.9,2.1Hz), 7.51 (d, 1H, J =5.2Hz), 8.03 (d, 1H, J=5.3Hz), 8.79 (br, 1H).

References