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US 2019/0194197 A1Published application
New processes for the preparation of vemurafenib
AssigneeFermion Oy
InventorAntti KATAJA
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Abstract
Novel processes are disclosed for manufacture of N-(3-(5-(4-chlorophenyl)-1 H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (I), wherein no protection-deprotection sequences or halogenation steps are required and use of palladium catalysts is minimized.
Claims20
A process for manufacture of a compound of formula (I):
- which process comprises:
- a) reacting a compound of formula (III):
- wherein R1 is C1-5 alkyl, C3-6 cycloalkyl, C3-5 alkenyl or optionally substituted benzyl, or sulfonyl, or carbonyl with either a compound of formula (IV);
- or a compound of formula (VI):
- wherein R2 and R3 are groups suitable for formation of a Vilsmeier reagent and A− is a suitable non-coordinating anion, to produce a compound of formula (IX) having a nitrile group:
- wherein R1 is as defined herein;
- and
- b) subjecting the compound of formula (IX) to removal of the R1 group and converting the nitrile group to a carboxylic acid, and performing a decarboxylation to produce a compound of formula (X):
- and
- c) reacting the compound of formula (X) with 2,6-difluoro-3-(propylsulfonamido)benzoic acid to give a compound of formula (I).
7 more elements
Dependencies are inferred from the claim text.