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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 448579Generated: October 25, 2026

Sodium hydride → 4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-2-methyl-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester

https://huagongshe.com/reaction/448579

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant5-(Methanesulfonyl)-2,3-dihydro-1H-indoleHCID 2736136—
Reactant4-(6-Chloro-2-methyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl esterHCID 86650176—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-2-methyl-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl esterHCID 58116597—

Reaction Conditions

Temperature90 °C

Reaction Steps

14a (100 mg) was dissolved in DMF with 5-methanesulfonyl-2,3-dihydro-1H-indole (0.3 mmol) and NaH (0.3 mmol). The mixture was heated at 90° C. for 4 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and water. The organic layer was washed with a saturated NaHCO3 solution, isolated, evaporated and purified by preparative HPLC to give 14-1, LCMS 475.1 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08481731B2
Source datasetuspto-grants-2013_07
ORD IDord-2c15132c73784c47bc92e879453f3492
Source noteuspto-grants-2013_07