2-Phenoxyethanamine → 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid (2-phenoxyethyl)amide

Participants

Reaction Steps

To a solution of 1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (Preparation 32, 50 mg, 0.31 mmol) in DMF (5 mL), was added 2-phenoxyethylamine (44 μL, 0.34 mmol), DIPEA (118 μL, 0.68 mmol) and HOBt (42 mg, 0.31 mmol) sequentially. The reaction mixture was stirred for 5 min prior to the addition of EDCI (42 mg, 0.22 mmol) in one portion. The resulting mixture was stirred for 20 h at rt and partitioned between ethyl acetate (50 mL) and water (20 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×30 mL). The combined organic fractions were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo to give an oil. Trituration with diethyl ether/isohexane and collection by filtration gave, after air-drying, the title compound as a cream coloured solid. δH (d6 DMSO): 3.48 (2H, m), 4.14 (2H, t), 6.94 (3H, m), 7.17 (1H, dd), 7.28 (3H, m), 7.77 (1H, d), 8.37 (1H, dd), 8.86 (1H, t); m/z (ES+)=282 [M+H]+; RT=2.60 min.

Provenance & Evidence