4-Azaindole → Pyrrolo[3,2-b]pyridin-1-ylamine

Beteiligte Stoffe

Reaktionsschritte

A solution of pyrrolo[3,2-b]pyridine (1.64 mmol) and potassium tert-butoxide (3.29 mmol) in DMF (7.3 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl. in ether (16.3 mL) is added drop-wise at rt and the reaction mixture is stirred at rt for 3 h. The reaction mixture is quenched with 5% Na2S2O3 aqueous solution (10 mL), and extracted with ether. The combined organic layer is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc to afford pyrrolo[3,2-b]pyridin-1-ylamine (136 mg, 62%) as a solid. MS: 134 (M+H); 1H NMR (300 MHz, CDCl3): δ 4.89 (br, 2N—H), 6.61 (d, H), 7.16 (m, H), 7.38 (d, H), 7.76 (d, H), 8.47 (d, H).

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