C(OC(=O)[NH:7][NH2:8])(C)(C)C.C(O)(=O)C.F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([C:23]1[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=1)=O.C1CCN2C(=NCCC2)CC1>CO.C1COCC1>[CH3:30][S:29][C:25]1[N:24]=[C:23]([C:21]2[C:16]3[C:15](=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:8][N:7]=2)[CH:28]=[CH:27][N:26]=1tert-Butylcarbazate (899 mg, 6.8 mmol) and acetic acid (0.5 mL) were added to a mixture of (2-fluoro-phenyl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone (840 mg, 3.4 mmol) in MeOH. The resulting mixture was heated at reflux for 16 h; it was then cooled to RT and partitioned between EtOAc and aqueous sodium bicarbonate. The organic layer was separated and dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was placed in a sealed tube with DBU (0.79 mL, 5.3 mmol) and THF. The resulting mixture was heated to 150° C. in a microwave reactor for 30 minutes. The reaction mixture was then evaporated under reduced pressure and the crude residue was purified by flash chromatography (hexane/EtOAc, 4/1) to afford 525 mg of 3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole.
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