Method for producing 1, 3-dialkylpyridinium oligomers and related compounds using a solid support

The method of producing a linear di-substituted pyridinium compound, the method comprising the steps of:

• (a) attaching a first pyridine compound selected from the group consisting of a 2-substituted pyridine compound, a 3-substituted pyridine compound and 4-substituted pyridine compound of the formula NC5R4—R′—X (1) to a solid support, to form a compound of the formula NC5R4—R′—Y-SUPPORT (2), wherein SUPPORT represents the solid support, R is selected from the group consisting of hydrogen, hydroxyl, and substituted and unsubstituted alkyl, alkoxy, aryl, alkaryl, aralkyl, and alkenyl groups, R′ is a first linking group, X is a group which can react with the solid support to attach the first pyridine compound to the support, and Y is selected from the group consisting of a direct bond and a second linking group;
• (b) forming a di-substituted pyridine compound of the formula −A-+NC5R4—R′-Z (3) from a second pyridine compound selected from the group consisting of a 2-substituted pyridine compound of formula (1), a 3-substituted pyridine compound of formula (1) and a 4-substituted pyridine compound of formula (1), which second pyridine compound may be selected from the group consisting of the same pyridine compound as the first pyridine compound and a different pyridine compound from the first pyridine compound, wherein A is a protecting group, and Z is a leaving group;
• (c) reacting the compound of formula (2) formed in step (a) with the compound of formula (3) formed in step (b), to form a di-substituted pyridinium compound of the formula −A-+NC5R4—R′-[−Q+NC5R4—R′—]nY-SUPPORT (4), wherein Q− is a counter ion and n=1;
• (d) optionally, repeating step (c) as many times as required to obtain a compound of formula (4) wherein n is an integer of ≧2;
• and
• (e) detaching the compound of formula (4) from the solid support, and reducing to form a di-substituted pyridinium compound of the formula NC5R4—R′-[−Q+NC5R4—R′—]n—X (5), wherein n is an integer, and Q− and X are a counter ion and a group which can react with the solid support to attach the first pyridine compound to the support respectively, which may be selected from the group consisting of the same Q and X as defined above in steps (c) and (a) respectively and different Q and X as defined above in steps (c) and (a) respectively.