HCID 90041030, compound → HCID 90041190, compound

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.

1. temperatureThe mixture was cooled
2. filtrationthen filtered through a pad of celite
3. concentrationthe filtrate was concentrated in vacuo
4. additionThe residue was diluted with THF (35 mL) and 1 N NaOH solution (18 mL)
5. stirringThe resulting mixture was stirred at room temperature for 16 h
6. concentrationconcentrated in vacuo to ˜20 mL
7. additionadjusted to pH7 by addition of 1N HCl
8. extractionThe mixture was extracted with ethyl acetate (100 mL×3)
9. customdried
10. concentrationconcentrated

ORD record

ord-b7d6dcc321ed49f488a34057f23d42b7

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334278B2