CCN(C(C)C)C(C)C.F[C:11]1[C:19]([F:20])=[C:18]([F:21])[CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14].[CH3:22][NH:23][CH2:24][CH2:25][OH:26].[H-].[Na+]>C(Cl)Cl.CO.O>[F:21][C:18]1[CH:17]=[CH:16][C:12]2[C:13](=[O:14])[N:23]([CH3:22])[CH2:24][CH2:25][O:26][C:11]=2[C:19]=1[F:20]
DIPEA (0.68 mL, 3.9 mmol) was added to a solution of 2,3,4-trifluorobenzoyl chloride (500 mg, 2.6 mmol) in DCM (5 mL) followed by the addition of N-methylethanolamine (0.31 mL, 3.9 mmol). The mixture was stirred for 20 hours. The solution was diluted with methanol (10 mL) and passed through an ISOLUTE® SCX-2 SPE column. The solution was evaporated. The residue was dissolved in DMF and sodium hydride (60% dispersion in mineral oil, 0.11 g, 2.7 mmol) was added portionwise over 5 minutes. The resulting mixture was stirred for 20 hours. Water (100 mL) was added dropwise and the mixture was extracted with ether (3×200 mL). Combined ethereal extracts were dried (MgSO4) and evaporated. The residue was purified by column chromatography (eluting with 1:1 ethyl acetate:isohexane to neat ethyl acetate) to afford the title compound (117 mg, 20%) as a colourless solid.
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