tert-butyl 4-(4-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate → 3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-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-(4-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (108 mg, 0.197 mmol) was deprotected in TFA/toluene (5/5 ml). This afforded 30 mg (27% yield) of the titled. 1H NMR (CD3OD, 300 MHz): δ 8.627-8.622 (d, 1H), 8.56 (s, 1H), 8.20 (s, 1H), 7.94 (s, 1H), 7.75-7.71 (m, 3H), 7.44-7.42 (d, 2H), 7.25-7.20 (t, 1H), 7.13-7.07 (m, 3H), 5.37 (s, 2H), 3.55-3.51 (d, 2H), 3.21-3.13 (m, 2H), 3.03-2.94 (m, 1H), 2.31 (s, 3H), 2.14-2.10 (d, 2H), 2.03-1.89 (qd, 2H). MS: m/z=448.4 (M+1), HPLC: 98.27% in method A.

Provenance & Evidence