Phthalylglycine aldehyde → HCID 69482477, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate (1.50 g, 5.47 mmol) and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetaldehyde (2.27 g, 12 mmol) under nitrogen in glacial acetic acid (50 mL) was treated with sodium triacetoxyborohydride (2.56 g, 12.1 mmol) at ambient temperature. After stirring for 30 min., 40 mL of glacial acetic acid (40 mL) was added, to dilute the reaction, followed by 0.17 g of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetaldehyde and 0.45 g sodium triacetoxyborohydride. After stirring another 2½ h, the reaction was heated to 45° C. for another hour. The reaction was evaporated in vacuo and the residue was triturated with water (500 mL), filtered, and washed with water. The resulting solid was dissolved in CH2Cl2 dried over MgSO4, filtered and evaporated in vacuo. The residue was dissolved in CH2Cl2 and chromatographed on silica gel eluting with 0-50% EtOAc in hexanes to provide the product as an solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (t, J=7.1 Hz, 3 H), 3.5 (q, J=6.2 Hz, 2 H), 3.8 (t, J=6.0 Hz, 2 H), 3.9 (s, 2 H), 4.2 (q, J=7.0 Hz, 2 H), 7.1 (ddd, J=9.1, 6.9, 1.8 Hz, 2 H), 7.3 (m, 3 H), 7.6 (t, J=6.2 Hz, 1 H), 7.7 (d, J=1.6 Hz, 1 H), 7.8 (m, 4 H); ES+MS: 447 (M+H+).

Provenance & Evidence