Aluminium lithium hydride → 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropan-1-amine

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Reaction Steps

(h)(i) 2-(4-(1-(4-Fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide (23 mg, 0.06 mmol) in 3 mL THF was treated with LiAlH4 (0.2 mL of 1.0 M solution in THF) and stirred for 18 h. The reaction was quenched with EtOAc, TFA was added, and the reaction was purified by HPLC to give 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropan-1-amine. (M+H)+=368. This material was coupled to 3,3,3-trifluoropropionic acid using General Coupling Method A. After 16 h, the reaction was purified by HPLC to give 6 mg of 3,3,3-trifluoro-N-(2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropyl)propanamide. (M+H)+=478.

Provenance & Evidence