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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 531797Generated: October 30, 2026

Lithium Hydroxide → 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetonitrile

https://huagongshe.com/reaction/531797

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium HydroxideHCID 3939—
Reactant2-(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) acetonitrileHCID 90031508—
Reactant3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochlorideHCID 118524085—
SolventMethanol tetrahydrofuran waterHCID 21892291—
Product2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetonitrileHCID 7294475333.3%

Reaction Steps

Using similar reaction conditions as described in step-iii of example-1, 2-(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) acetonitrile (60 mg, 0.092 mmol) was hydrolyzed by lithium hydroxide (8 mg, 0.185 mmol) in THF/methanol/water (5/1/1 ml) to yield 15 mg (33.3% yield) of the titled compound. 1H NMR (CDCl3, 400 MHz): δ 9.19 (s, 1H), 8.50-8.47 (dd, 2H), 8.128-8.123 (d, 1H), 7.86 (s, 1H), 7.79-7.76 (dd, 1H), 7.70 (s, 1H), 7.447-7.441 (d, 1H), 7.35-7.30 (m, 1H), 7.10-6.90 (m, 3H), 6.80-6.78 (d, 1H), 5.39 (s, 2H), 3.70-3.67 (t, 4H), 3.61 (s, 2H), 2.76-2.74 (t, 4H). MS: m/z=493.4 (M+1), HPLC: 97.07% in method A.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353107B2
Source datasetuspto-grants-2016_05
ORD IDord-a35c80e5746943308b4b4b58b2f600a7
Source noteuspto-grants-2016_05