Facile condensation of methylbenzoxazoles with aromatic aldehydes
AssigneeMerck & Co., Inc.
InventorsRalph P. Volante, Joseph E. Lynch, Ioannis Houpis, Audrey Molina
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Abstract
An efficient process for the preparation of styrylbenzoxazoles and derivatives thereof comprises reacting a methylbenzoxazole with an aromatic aldehyde in the presence of strong base at low temperature, followed by warming. The condensation products are inhibitors of H.sup.+ K.sup.+ -ATPase, and are also useful as penultimate compounds in the preparation of inhibitors of HIV reverse transcriptase.
Claims2
The process of synthesizing the product compound 3-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-benzoxy-pyridine of the structure ##STR5## comprising the step of (a) mixing about four equivalents of 2-methylbenzoxazole with about one equivalent of 2-benzoxy-5-ethyl-6-methylnicotinaldehyde, yielding a mixture;
- (b) mixing, at a temperature of about -50.degree. C., said mixture with about 1.2 equivalents of potassium tert-butoxide;
- (c) warming the reaction mixture to give the product compound
- said process having a yield of 95% or greater.
The process of synthesizing the product compound 3-[2-(benzoxazol-2-yl-ethyl]-5-ethyl-6-methyl-2-(1H)-pyridinone, of the structure ##STR6## comprising the steps of (a) mixing about four equivalents of 2-methylbenzoxazole with about one equivalent of 2-benzoxy-5-ethyl-6-methylnicotinaldehyde, yielding a mixture;
- (b) mixing, at a temperature of about -50.degree. C., said mixture with about 1.2 equivalents of potassium tert-butoxide;
- (c) warming the reaction mixture to give the olefin intermediate compound;
- and
- (d) hydrogenating to give the product compound,
- the steps of (a)-(c) having an overall yield of 95% or greater.
Dependencies are inferred from the claim text.