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

Participants

Reaction Steps

To a stirred solution of the crude azaindole 8 (0.64 mmol) in MeOH (6 mL) was added a 10% solution of HCl in methanol (3 mL). After 20 min the mixture was concentrated and partitioned between AcOEt and saturated aqueous NaHCO3 solution. The aqueous layer was extracted with AcOEt (2×) and the combined organic solutions were dried (MgSO4), filtered and concentrated. The residue was purified by PTLC using 5% MeOH in CH2Cl2 to afford the desired methyl derivative 9 (68 mg, 81% over 3 steps). 1H NMR (400 MHz; CDCl3) δ 2.45 (s, 3H), 6.42 (d, J=3.4 Hz, 1H), 7.34 (d, J=3.4 Hz, 1H), 7.76 (d, J=1.7 Hz, 1H), 8.19 (d, J=1.7 Hz, 1H), 10.92 (br s, NH).

Provenance & Evidence