[CH:1]([N:4](CC)[CH:5](C)C)(C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[C:18](O)=[O:19])=[C:13]([F:22])[CH:12]=1.CNC.C1COCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[C:18]([N:4]([CH3:5])[CH3:1])=[O:19])=[C:13]([F:22])[CH:12]=1N,N-Diisopropylethylamine (0.8 g, 0.006 mol) was added to a mixture of (4-bromo-2-fluorophenyl)(hydroxy)acetic acid (Oakwood, Cat. No. 019267) (0.5 g, 0.002 mol), dimethylamine in THF (2.4 mmol, 2.0 M, 1.2 mL), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.1 g, 0.0024 mol) in methylene chloride (10 mL). The mixture was stirred at r.t. overnight, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-40%) to afford the desired product. LCMS (M+H)+=276.2/278.2. 1H NMR (300 MHz, DMSO-d6) δ: 9.50 (d, J=1.1 Hz, 1H), 7.97 (dd, J=8.0, 1.5 Hz, 1H), 7.83 (dd, J=11.4, 1.5 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.51 (d, J=1.1 Hz, 1H), 7.01 (s, 1H), 5.70 (s, 1H), 5.65 (s, 1H), 3.96 (s, 6H), 2.94 (s, 3H), 2.88 (s, 3H).
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