Br[C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][C:10]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]([CH2:28][C:29]([OH:31])=[O:30])[CH:24]=[C:25]([Cl:27])[CH:26]=3)([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9][CH2:8]2)=[N:4][CH:3]=1.[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[Cl:27][C:25]1[CH:24]=[C:23]([CH2:28][C:29]([OH:31])=[O:30])[CH:22]=[C:21]([O:20][CH2:19][CH2:18][C:10]2([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:11][CH2:12][N:7]([C:5]3[S:6][C:2]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]([F:32])[CH:38]=4)=[CH:3][N:4]=3)[CH2:8][CH2:9]2)[CH:26]=1A mixture of [3-[2-[1-(5-bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid (60 mg), 3-fluorophenyl boronic acid (32 mg), tetrakis (triphenylphosphine) palladium (13 mg), 1M sodium carbonate (0.55 mL) and dimethylformamide (1 mL) was reacted with a microwave reaction device at 180° C. for 5 minutes. The insoluble material was filtrated. To the filtrate was added formic acid. The solvent was evaporated under reduced pressure and the residue was purified by high performance liquid chromatography to give the title compound (14.4 mg). Yield: 24%.
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