HCID 90041030, compound → HCID 90041190, compound

Participants

Reaction Steps

To a stirred suspension of (2-bromo-3-chloro-7-hydroxymethyl-pyrrolo[2,3-b]pyrazin-5-yl)-methanol (2.0 g, 6.84 mmol) in acetone (67 mL) was added Jone's reagent (2.12 mL) and the mixture stirred at room temperature for 20 min. The mixture was cooled then filtered through a pad of celite and the filtrate was concentrated in vacuo. The residue was diluted with THF (35 mL) and 1 N NaOH solution (18 mL). The resulting mixture was stirred at room temperature for 16 h, then concentrated in vacuo to ˜20 mL and adjusted to pH7 by addition of 1N HCl. The mixture was extracted with ethyl acetate (100 mL×3), dried and concentrated to give 2-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (1.4 g, 80%) as a brown solid. LC-MS: 260.2 (M−H). This was used directly without further purification.

Provenance & Evidence