Lithium Hydroxide → (S)-1-(4-(4-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazin-1-yl)propan-2-ol

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Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, (S)-1-(4-(4-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)propan-2-ol (100 mg, 0.151 mmol) was hydrolyzed with lithium hydroxide (13 mg, 0.302 mmol) in THF/methanol/water (5./1/1 mL) to yield 33 mg (35.1% yield) desired product. 1H NMR (CD3OD, 400 MHz): δ 8.667-8.663 (d, 1H), 8.55-8.54 (d, 1H), 8.22 (s, 1H), 7.95 (s, 1H), 7.77 (s, 1H), 7.69-7.66 (d, 2H), 7.25-7.21 (t, 1H), 7.17-7.08 (m, 5H), 5.37 (s, 2H), 4.30-4.20 (m, 1H), 4.00-3.80 (m, 2H), 3.75-3.60 (m, 2H), 3.30-3.10 (m, 6H), 2.31 (s, 3H), 1.29-1.27 (d, 3H). MS: m/z=507.65 (M+1), HPLC: 91.66% in method A.

Provenance & Evidence