Lithium Hydroxide → 3-(1-(3-fluorobenzyl)-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-iii of example-1, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride (170 mg, 0.026 mmol) was hydrolyzed by lithium hydroxide (12 mg, 0.264 mmol) in THF/methanol/water (10/5/2.5 ml) to yield 60 mg (40% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.54 (s, 2H), 8.229-8.227 (d, 1H), 7.959-7.957 (d, 1H), 7.73-7.70 (m, 3H), 7.44-7.41 (d, 2H), 7.38-7.23 (m, 1H), 7.12-7.09 (d, 1H), 7.08-7.00 (m, 2H), 5.43 (s, 2H), 3.55-3.50 (d, 2H), 3.21-3.13 (m, 2H), 3.05-2.93 (m, 1H), 2.16-2.11 (d, 2H), 2.02-1.89 (m, 2H). MS: m/z=452.5 (M+1), HPLC: 96.75% in method A.

Provenance & Evidence