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With toluene-4-sulfonic acid; In tetrahydrofuran; for 18h;Inert atmosphere; Reflux;
Referential example 25 (l-(Tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-lH-indazol-4-yl)methanamine (127) step 1 : A round-bottom flask was charged with 4-bromo-6-(trifluoromethyl)-lH-indazole (1.00 g, 3.8 mmol), TsOH monohydrate (27 mg, 0.15 mmol), 3,4-dihydro-2H-pyran (1.59 g, 18.9 mmol), and THF (25 mL). The reaction mixture was degassed with nitrogen and heated under reflux for 18 h, and then the solvent was removed in vacuo. The residue was purified by S1O2 chromatography to afford 4-bromo-l - (tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-lH-indazole (1.03 g, 78percent) as a yellow oil. MS (ESI) m/z: 265.2 [(M - THP group)+l]+.
(4-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid[ No CAS ]
[ 1000342-95-9 ]
[ 76-05-1 ]
[ 1454293-91-4 ]
Yield
Reaction Conditions
Operation in experiment
30%
EXAMPLE 130: N-(2-hydroxyethyl)-4-(6-(trifiuoromethyl)-lH-indazol-4- yl)benzamide [0550] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.300 g, 1.132 mmol), (4-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid (0.237 g, 1.132 mmol) and PdCl2(dppf) (0.041 g, 0.057 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting yellow suspension was heated at 140°C for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 40percent> ACN (containing 0.035percent) TFA) in H20 (containing 0.05percent TFA) over a period of 4.5 minutes. The product-containing fractions were combined and volatiles removed in vacuo to give a TFA salt of the title compound as white solid (0.12 g, 30percent). 1H NMR (400 MHz, CD3OD) delta ppm 3.56 (t, J=5.81 Hz, 2 H), 3.75 (t, J=5.81 Hz, 2 H), 7.49 (d, J=1.01 Hz, 1 H), 7.78-7.89 (m, 2 H), 7.93 (s, 1 H), 8.00-8.10 (m, 2 H), 8.21-8.32 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci7Hi4F3N302, 350.1; found 350.1.
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