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With phosphorus tribromide; In diethyl ether; at 20℃;
Phosphorus tribromide (0.230 ml, 2.45 mmol) is added to a stirred solution of (1-methyl-1 H- 1 ,2,3-benzotriazole-5-yl)methano. (0.4 g, 2.45 mmol) in diethyl ether (25 mi) under an inert atmosphere of Argon. After stirring overnight at room temperature, the reaction mixture is diluted with water (5 ml) and stirred vigorously for 10 minutes. The organic portion is <n="64"/>separated, washed with water (2 x 5 ml), brine (2 x 5 ml) and concentrated in vacuo to yield the titled product which is used crude in the next step. (MH+ 226).
With phosphorus tribromide; In diethyl ether; at 20℃;
5-Bromomethyl-1-methyl-1 H-benzotriazole: Phosphorus tribromide (0.230 ml, 2.45 mmol) is added to a stirred solution of (I -methyl-I H- 1,2,3-benzotriazole-5-yl) methanol (0.4 g, 2.45 mmol) in diethyl ether (25 ml) under an inert atmosphere of Argon. After stirring overnight at room temperature, the reaction mixture is diluted with water (5 ml) and stirred vigorously for 10 minutes. The organic portion is separated, washed with water (2 x 5 ml), brine (2 x 5 ml) and concentrated in vacuo to yield the titled product which is used crude in the next step. (MH+ 226).
With triethylamine; In dichloromethane; at 5 - 10℃; for 2.5h;
Methanesulfonyl chloride (0.0046 mol) was added at 5C to a mixture of 1 -methyl- IH- benzotriazole-5 -methanol (0.0031 mol) and triethyl amine (0.0092 mol) in DCM (50ml) under N2 flow. The mixture was stirred at 100C for 2 hours and 30 minutes, then evaporated to dryness, yielding intermediate 26. This product was used directly in the next reaction step.
With di-tert-butyl-diazodicarboxylate; PS-triphenylphosphine; In tetrahydrofuran; at 20℃; for 43.0h;
Example 255; 4-{3,5-dimethyl-1-[(1-methyl-1H-1,2,3-benzotriazol-5-yl)methyl]-1H-pyrazol-4-yl}benzonitrile A resin reagent (PS-triphenylphosphine) (about 87 mg) was charged in a miniblock reaction apparatus (Bohdan), and preconditioned therein. Then, a solution (0.15 mol/L, 0.75 mL) of <strong>[120321-72-4](1-methyl-1H-1,2,3-benzotriazol-5-yl)methanol</strong> in THF and a solution (0.15 mol/L, 0.50 mL) of 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzonitrile synthesized in Reference Example 5 in THF were added and the mixture was stirred. A solution (0.375 mol/L, 0.50 mL) of di-tert-butyl azodicarboxylate in THF was added and the mixture was stirred at room temperature for 43 hr. The resin reagent was removed by filtering and washing the reaction mixture. The filtrate was concentrated. The residue was purified by reversed-phase preparative HPLC (Gilson, UniPoint system, YMC ODS column 30×75 mm, 0.1% TFA containing acetonitrile-water (2:98-100:0)) to give the title compound (5.4 mg).MS (ESI+, m/e) 343 (M+1)
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