[OH:1][CH2:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][CH:4]=1.[Li]CCCC.[I:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C1COCC1>[I:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([O:1][CH2:2][C:3]2[NH:8][C:7](=[O:9])[CH:6]=[CH:5][CH:4]=2)=[O:21])=[CH:18][CH:17]=10.2021 g (1.615 mmol) of the 6-hydroxymethyl-2-pyridone was suspended in 15 mL of THF in a 100 mL RBF under the presence of argon gas and was placed in a −80° C. methanol bath. 1.03 mL (1.648 mmol) of BuLi was added dropwise to the reaction which was stirred for 20 min. 0.4374 grams (1.641 mmol) of 4-iodobenzoyl chloride was dissolved in 15 mL of THF and brought to −80° C. before being added dropwise to the reaction mixture. The reaction was allowed to stir at −80° C. for 48 hours before being warmed to room temperature. The reaction was quenched with 20 mL of water and extracted with ethyl acetate (4×20 mL), the organic layers combined and washed with brine (3×20 mL), and dried over MgSO4. The solvent was removed in vacuo to produce a brown solid. The product was purified by crystallization from toluene. The yield of the reaction was 0.032 g (5.58% Yield). MP: 206-208° C. IR (cm−1) 3426.48 (m, broad), υ (O—H), 3126.38 (m, broad), υ (N—H), 1722.45 (m), υ (C═O), 1656.57 (s), 1392.33 (m) υ (C═C aromatic). 1H NMR (DMSO-d6, 500 MHz) δ: 5.12 (s, 2H), 6.35 (d, J=9.1 Hz, 2H), 7.45 (t, J=7.0 Hz, 1H), 7.76 (d, J=4.8 Hz, 2H), 7.94 (d, J=9.0 Hz, 2H), 11.75 (s, 1H). HRMS: m/e, found 377.9598 (M+Na+). Calc. for C13H10INO3Na: 377.9603.
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