Lithium Hydroxide → (2S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-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, (2S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)propan-2-ol (165 mg, 0.238 mmol) was hydrolyzed with lithium hydroxide (100 mg, 2.38 mmol) in THF/methanol/water (20/10/5 mL) to yield 31 mg (13% yield) of desired product. 1H NMR (CD3OD, 300 MHz): δ 8.43-8.42 (d, 1H), 7.838-7.831 (d, 1H), 7.50-7.57 (d, 2H), 7.40-7.30 (m, 2H), 7.05-6.95 (m, 4H), 6.95-6.84 (m, 1H), 5.35 (s, 2H), 4.05-3.95 (m, 1H), 3.25-3.22 (t, 4H), 2.80-2.62 (m, 4H), 2.50-2.30 (m, 2H), 2.20 (s, 3H), 2.16 (s, 3H), 1.17-1.15 (d, 3H). MS: m/z=538.9 (M+1), HPLC: 95.51% in method A.

Provenance & Evidence