Hydrochloric Acid → HCID 86621121, compound

Participants

Reaction Steps

A solution of 9.76 g (54 mmol) of the compound from step I (1) dissolved in 100 mL of acetonitrile was treated with 11.5 g (81 mmol) of methyl iodide. The reaction solution was stirred for 16 h at rt, then concentrated to an oil. The crude imidazolium iodide was then redissolved in 70 mL of THF and 5.25 g (36 mmol) of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde from step I (2) was added, followed by triethylamine (72 mmol, 7.2 grams). The resulting solution was heated to 60° C. for 24 h, then cooled and poured into a solution of 0.1 N HCl. Ethyl acetate was added, and the organic layer was separated, dried with brine and concentrated. The crude product (12.3 g, 132%) of the desired title compound contained an unknown impurity which was removed at the next step. MS ESI (M+H)+=260.24. 1H NMR (500 MHz, CDCl3) δ ppm 0.76-1.06 (m, 3H) 1.18-1.35 (m, 2H) 1.43-1.57 (m, 2H) 1.58-1.81 (m, 2H) 2.97-3.19 (m, 3H) 7.29-7.32 (m, 1H) 8.13 (s, 1H) 8.45 (dd, J=4.73, 1.68 Hz, 1H) 8.58 (d, J=7.94 Hz, 1H) 10.03 (s, 1H)

Provenance & Evidence