Retrosynthetic analysis

July 24, 2024

• Title:       

  Retrosynthetic analysis

• Image Source:

  Development of a practical route for the manufacture of N-[5-(3-lmidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]acetamide

• Mark:

  Scheme 1

• Associated context:

  In a retrosynthetic plan, a sequential approach was designed where the imidazole would be introduced last via an SNAr on the activated aryl fluoride 2 (see Scheme 1). The thiazole subunit could come from the keto intermediate 3 and thiourea after  R-halogenation and condensation. Compound 3 could, in turn, come from an SNAr reaction of 3,4-difluorobenzaldehyde 4 with sodium thiomethoxide or more directly with the corresponding sulfinate anion, followed by Henry condensation with nitroet-  hane and subsequent reduction of the nitro compound.