Lithium Hydroxide → cyclopropyl(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)methanone

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Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, cyclopropyl(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)methanone (100 mg, 0.148 mmol) was hydrolyzed with lithium hydroxide (31 mg, 0.74 mmol) in THF/methanol/water (3/2/1 mL) to yield 42 mg (54.5% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.53 (s, 2H), 8.49-8.48 (d, 1H), 8.46-8.45 (d, 1H), 8.24 (s, 1H), 7.998-7.995 (d, 1H), 7.74 (s, 1H), 7.50-7.47 (d, 1H), 7.37-7.35 (m, 1H), 7.12-6.98 (m, 3H), 5.44 (s, 2H), 4.08-3.83 (m, 8H), 2.05-1.95 (m, 1H), 0.95-0.87 (m, 2H). MS: m/z=522.4 (M+1), HPLC: 96.90% in method A.

Provenance & Evidence