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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1909303Generated: October 31, 2026

Sodium Carbonate → HCID 68295713, compound

https://huagongshe.com/reaction/1909303

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant(3-hydroxyphenyl)boronic AcidHCID 2734359—
ReactantDichloromethane methanolHCID 21226129—
ReactantMethyl 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylateHCID 67468180—
CatalystHCID 178418397HCID 178418397—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 68295713HCID 6829571361%

Reaction Conditions

Temperature100 °C

Reaction Steps

A solution of methyl 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylate (1 g, 3.93 mmol), (3-hydroxyphenyl)-boronic acid (1.43 g, 4.72 mmol) and Pd(PPh3)4 (0.227 g, 0.196 mmol) in 1,4-dioxane (10.5 mL) was purged with argon for 10 min. Then, 2 M Na2CO3 solution (1.5 g, 14.2 mmol) was added to it and again argon was purged through it for 10 min. The reaction mixture was stirred at 100° C. for 1 h. After completion of the reaction, water was added to it and extraction was carried out using 5% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography over silica gel (60-120 mesh size) to afford the title compound (0.8 g, 61%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598167B1
Source datasetuspto-grants-2013_12
ORD IDord-991f61104ee543238b95b8745104a4d9
Source noteuspto-grants-2013_12