Lithium Hydroxide → (S)-1-(4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-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-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl) propan-2-ol (100 mg, 0.146 mmol) was hydrolyzed with lithium hydroxide (30 mg, 0.73 mmol) in THF/methanol/water (2/2/1 mL) to yield 45 mg (58.4% yield) of desired product. 1H NMR (CD3OD, 400 MHz): δ 8.54 (s, 2H), 8.27 (s, 1H), 7.98 (s, 1H), 7.74 (s, 1H), 7.60-7.53 (m, 2H), 7.45-7.35 (q, 1H), 7.25-7.21 (t, 1H), 7.14-7.12 (d, 1H), 7.09-7.00 (m, 2H), 5.45 (s, 2H), 4.30-4.20 (m, 1H), 3.76-3.55 (m, 4H), 3.50-3.30 (m, 2H), 3.29-3.15 (m, 4H), 1.29-1.27 (d, 3H). MS: m/z=529.6 (M+1), HPLC: 98.28% in method A.

Provenance & Evidence