[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O>[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][CH2:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]
To a stirred solution of methyl 3-formylbenzoate (1 g, 6.092 mmol) in anhydrous DCM (30 mL) was added 2-fluoroaniline (0.620 mL, 6.396 mmol) followed by glacial acetic acid (0.350 mL, 6.092 mmol). The reaction was stirred at room temperature for 18 hours. Sodium triacetoxyborohydride (3.23 g, 15.23 mmol) was added, and the reaction was stirred at room temperature for 3 hours. Water was added to quench the reaction, and the mixture was diluted with DCM. The organic layer was washed with brine, passed through a hydrophobic fit and the solvent was removed in vacuo to afford the title compound as a yellow oil (1.57 g, quantitative yield).
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