3-Aminopropylphosphonic acid → (3-{[6-(5-Hexyl-pyridin-2-yl)-biphenyl-3-ylmethyl]-amino}-propyl)-phosphonic acid

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To a solution of 6-(5-hexylpyridin-2-yl)biphenyl-3-carbaldehyde (80 mg, 0.233 mmol) and (3-aminopropyl)phosphonic acid (32.4 mg) in methanol was added tetrabutylammonium hydroxide (1M in MeOH, 0.23 mL). The reaction mixture was heated to 50° C. for 30 min with stirring, then sodium cyanoborohydride (41 mg, 0.65 mmol) was added. The reaction mixture was heated to 50° C. with stirring for 3 h. After cooling to RT, the mixture was concentrated and purified by MPLC (0-100% ethyl acetate in hexanes) to give 36 mg of the desired product as a colorless solid. 1H NMR (300 MHz, CD3OD) δ 8.34 (d, J=1.76 Hz, 1H), 7.58-7.63 (m, 3H), 7.41 (dd, J=2.34, 8.20 Hz, 1H), 7.20-7.25 (m, 3H), 7.11-7.16 (m, 2H), 6.91 (d, J=7.91 Hz, 1H), 4.21 (s, 2H), 3.11 (t, J=6.30 Hz, 2H), 2.61 (t, J=7.62 Hz, 2H), 1.92-2.07 (m, 2H), 1.55-1.74 (m, 4H), 1.31 (br. s., 6H), 0.86-0.92 (m, 3H).

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