Lithium Hydroxide → (S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-5-methyl-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-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)propan-2-ol (200 mg, 0.29 mmol) was hydrolyzed with lithium hydroxide (37 mg, 0.88 mmol) in THF/methanol/water (6/4/2 mL) to yield 10 mg (6.4% yield) after purification by preparative HPLC along with one more isomer example 130. 1H NMR (CDCl3, 300 MHz): δ 9.12 (s, 1H), 8.548-8.542 (d, 1H), 8.02-8.01 (d, 1H), 7.59 (s, 1H), 7.54-7.51 (d, 2H), 7.36-7.29 (m, 2H), 7.26-6.91 (m, 5H), 5.32 (s, 2H), 3.95-3.90 (m, 1H), 3.30-3.23 (m, 4H), 2.90-2.86 (m, 2H), 2.62-2.60 (m, 2H), 2.43-2.31 (m, 5H), 1.19-1.17 (d, 3H). MS: m/z=524.9 (M+1), HPLC: 95.68% in method A.

Provenance & Evidence