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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1054879Generated: November 1, 2026

Hydrochloric Acid → 6-chloro-5-[6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl]-1H-indole-3-carboxylic acid

https://huagongshe.com/reaction/1054879

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium HydroxideHCID 14798—
ReactantMethyl 6-chloro-5-(6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl)-1h-indole-3-carboxylateHCID 86698855—
SolventMethanolHCID 887—
Product6-chloro-5-[6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl]-1H-indole-3-carboxylic acidHCID 8669885637.5%

Reaction Conditions

Temperature80 °C

Reaction Steps

A vial was charged with methyl 6-chloro-5-[6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl]-1H-indole-3-carboxylate (52.5 mg, 0.130 mmol), NaOH aqueous (2 mL, 2M) and methanol (2 mL). The mixture was heated at 80° C. for 3 hrs. The mixture was cooled to room temperature and neutralized with conc. HCl aqueous to pH=6. The mixture was evaporated to dryness, and the resulting residue was purified through prep. HPLC to give the title compound (18.9 mg, 37.3%) as off-white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09394285B2
Source datasetuspto-grants-2016_07
ORD IDord-cb51e566e4d045d09314e62a5076f469
Source noteuspto-grants-2016_07