Hydrochloric Acid → 5-bromo-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a stirred solution of the TBS derivative 26 (1.01 g, 3.3 mmol) in MeOH (10 mL) was added a 10% solution of HCl in MeOH (7 mL). After 8 min the solvents were evaporated and the residue was partitioned between AcOEt and saturated aqueous NaHCO3. The aqueous layer was extracted with AcOEt (3×). The combined organic solutions were dried (MgSO4), concentrated and purified by PTLC with CH2Cl2:MeOH=95:5 as eluent to afford the bromo derivative 27 (0.60 g, 94%). 1H NMR (400 MHz; CDCl3) δ 6.47 (dd, J=2.0, 3.5 Hz, 1H), 7.37 (dd, J=2.5, 3.5 Hz, 1H), 8.08 (d, J=2.0 Hz, 1H), 8.36 (d, J=2.0 Hz, 1H), 10.24 (br s, H).

Provenance & Evidence