CCN(C(C)C)C(C)C.[NH2:10][C:11]1[C:12]([F:23])=[C:13]([CH2:20][CH2:21][OH:22])[C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1.[C:24](Cl)(=[O:26])[CH3:25]>C1COCC1>[C:24]([O:22][CH2:21][CH2:20][C:13]1[C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=[C:11]([NH2:10])[C:12]=1[F:23])(=[O:26])[CH3:25]To a solution of DIEA (1.80 mL, 10.6 mmol) and 2-(3-amino-2-fluoro-6-nitrophenyl)ethanol (0.88 g, 4.40 mmol), as prepared in the preceding step, in THF (10 mL) in an ice-bath was added a solution of acetyl chloride (319 μL, 4.49 mmol) in THF (5 mL). After stirring for 1.5 hour, the ice-bath was removed and the mixture was continued to stir at ambient temperature overnight. Additional acetyl chloride (63 μL, 0.88 mmol) was added, and the mixture was stirred for another 16 hours. The solvents were removed, and the mixture was partitioned between DCM and H2O. The organic layer was separated, and the aqueous layer was back-extracted with DCM. The organic layers were combined, washed with H2O (twice), dried over Na2SO4, concentrated, and flash chromatographed on silica gel eluting with EtOAc/DCM (0, 1, 2, and 5%) to give the title compound (0.73 g, 69% yield) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ 7.85 (dd, J=9.0, 1.5 Hz, 1H), 6.68 (t, J=8.9 Hz, 1H), 4.38-4.35 (m, 4H), 3.38 (dt, J=6.6, 2.8 Hz, 2H), 2.03 (s, 3H).
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