Lithium Hydroxide → (S)-1-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl) 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-(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) propan-2-ol (90 mg, 0.135 mmol) was hydrolyzed with lithium hydroxide (14 mg, 0.270 mmol) in THF/methanol/water (5/2/1 mL) to yield 52 mg (63.0% yield) of desired product. 1H NMR (CD3OD, 400 MHz): δ 8.56-8.55 (d, 1H), 8.485-8.481 (d, 1H), 8.44-8.43 (d, 1H), 8.24 (s, 1H), 8.09-8.06 (dd, 1H), 7.98 (s, 1H), 7.71 (s, 1H), 7.40-7.38 (q, 1H), 7.13-7.11 (m, 2H), 7.10-7.00 (m, 2H), 5.45 (s, 2H), 4.70-4.40 (bs, 2H), 4.30-4.20 (m, 1H), 3.90-3.50 (bs, 4H), 3.17-3.11 (m, 2H), 1.30-1.27 (m, 3H). MS: m/z=512.3 (M+1), HPLC: 98.72% in method A.

Provenance & Evidence