tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate → 5-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (82 mg, 0.145 mmol) was deprotected in methanol/HCl in dioxane (5/5 mL) to afford 8.2 mg (12.2% yield) of the titled compound after purification by preparative TLC using 8% methanol in chloroform as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.448-8.442 (d, 1H), 8.098-8.091 (d, 1H), 7.839-7.837 (d, 1H), 7.73 (s, 1H), 7.54 (s, 1H), 7.48-7.38 (m, 3H), 7.26-7.12 (m, 5H), 7.44-7.41 (t, 2H), 3.37-3.31 (m, 1H), 3.19-3.15 (t, 3H), 3.03-2.93 (td, 2H), 1.97-1.88 (m, 5H). MS: m/z=466.5 (M+1), HPLC: 98.63% in method A.

Provenance & Evidence