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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2275208Generated: November 1, 2026

Potassium Hydroxide → 9-Hydroxy-3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

https://huagongshe.com/reaction/2275208

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium HydroxideHCID 14797—
Reactant1,4-DioxaneHCID 31275—
ReactantDi-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 11618717—
Reactant3-Chloro-9-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 66834320—
SolventWaterHCID 962—
Product9-Hydroxy-3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 66834021—

Reaction Conditions

Temperature60 °C

Reaction Steps

9-Bromo-3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound S7-1, 30 mg, 0.06 mmol) was dissolved in the mixture solvent of water.dioxane (1:1) (0.5 mL), added with tris(benzylidenacetone dipalladium)chloroform complex (3.1 mg, 0.05 eq.), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (2.5 mg, 0.1 eq.) and KOH (0.5 N aqueous solution 180 μL, 1.5 eq.), and stirred at 60° C. for 12 hr. After cooling, the reaction solution was concentrated under reduced pressure, and the resulting residues were purified by HPLC to obtain the title compound (white solid, 4.6 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09126931B2
Source datasetuspto-grants-2015_09
ORD IDord-a215bc3a91bb4097b97061613c4f4a8c
Source noteuspto-grants-2015_09