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US 8,946,425 B2Granted
Processes and intermediates for producing azaindoles
AssigneeVertex Pharmaceuticals Incorporated
InventorsGerald J. Tanoury, Young Chun Jung, Derek Magdziak, Adam Looker, Billie J. Kline, Václav Jur{hacek over (c)}ík, Beatriz Dominguez Olmo
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Abstract
The present invention relates to processes and intermediates for the preparation of compounds useful as inhibitors of Janus kinases (JAK).
Claims22
A process for preparing a compound of Formula 1:
- or a pharmaceutically acceptable salt thereof, wherein R1 is —H, —Cl or —F;
- comprising the steps of:
- iva) reacting a compound of Formula 5 with bromine in an organic solvent to generate a compound of Formula 6:
- va) reacting the compound of Formula 6 with p-toluenesulfonyl chloride to generate a compound of Formula 7:
- vi) reacting the compound of Formula 7 with triisopropyl borate, in the presence of an organic solvent and a strong lithium base to generate a compound of Formula 8:
- and vii) esterifying the compound of Formula 8 with pinacolate alcohol in an organic solvent to generate a compound of Formula 1.
3 more elements
A process for preparing a compound of Formula 1:
- or a pharmaceutically acceptable salt thereof, wherein R1 is —H, —Cl or —F;
- comprising the steps of:
- ivb) reacting a compound of Formula 5 with p-toluenesulfonyl chloride to generate a compound of Formula 9:
- vb) reacting the compound of Formula 9 with N-bromosuccinimide to generate a compound of Formula 7
- vi) reacting the compound of Formula 7 with triisopropyl borate, in the presence of an organic solvent and a strong lithium base to generate a compound of Formula 8:
- and vii) esterifying the compound of Formula 8 with pinacolate alcohol in an organic solvent to generate a compound of Formula 1.
3 more elements
Dependencies are inferred from the claim text.