[CH3:1][N:2]1[C:6](B(O)O)=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[NH2:14][C:15]1[S:16][C:17](Br)=[CH:18][N:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:1][N:2]1[C:6]([C:17]2[S:16][C:15]([NH2:14])=[N:19][CH:18]=2)=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1A suspension of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)boronic acid (290 mg, 1.5 mmol), 2-amino-5-bromothiazole (1 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (A-Phos) (53 mg) and K3PO4 (212 mg, 1 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 70° C. for 1 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. Prep HPLC purification furnished 4.6 mg 5-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole-2-ylamine (63) as light yellow solid (yield 1.9%; purity>95%).
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