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

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Reaction Steps

The crude mixture containing 11 (5.38 g) was treated with MeOH (48 mL) and 10% aq. HCl (97 mL) for 0.5 h. The acid was neutralised by dropwise addition of sat. aqueous NaHCO3. The resulting solid was filtered off, washed with water (3×), dried in vacuum and extracted with CH2Cl2. The extracts were concentrated to afford a dark red oil, which was purified by SGC with CH2Cl2:MeOH as eluent (gradient elution up to 99:1, v/v) to give 12 as a brown oil (1.23 g, 37% over 2 steps); 1H NMR (400 MHz, CDCl3) δ 0.90 (t, J=7.3 Hz, 3H), 1.35-1.50 (m, 2H), 1.52-1.65 (m, 2H), 2.87 (t, J=7.4 Hz, 2H), 6.49 (dd, J=3.5, 1.8 Hz, 1H), 7.41 (dd, J=3.4, 2.3 Hz, 1H), 8.10 (d, J=2.0 Hz, 1H), 8.43 (d, J=2.0 Hz, 1H), 10.90-11.10 (bs, NH).

Provenance & Evidence