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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 473021Generated: October 29, 2026

Cesium carbonate → Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate

https://huagongshe.com/reaction/473021

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantN-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-methylpropane-2-sulfinamideHCID 58198087—
CatalystHCID 178418476HCID 178418476—
Solvent1,4-DioxaneHCID 31275—
ProductEthyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylateHCID 5819776730%

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of compound 5 (100 mg, 0.3 mmol), compound 5A (89 mg, 0.6 mmol), Cs2CO3 (2 M, 0.45 mL) and Pd(PPh3)2Cl2 (10 mg) in 1,4-dioxane (5 mL) under a nitrogen atmosphere was stirred in microwave at 120° C. for 15 min. The reaction mixture was concentrated in vacuo to give the residue, which was purified pre-TLC to give compound 6 (40 mg, yield 30%) as a white solid. 1H NMR (CDCl3 400 MHz): δ 8.05 (m, 1H), 7.87 (m, 3H), 7.72 (m, 3H), 7.60 (m, 1H), 3.69-3.75 (m, 2H), 3.17 (m, 2H), 3.01 (m, 2H), 2.30 (m, 4H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08633212B2
Source datasetuspto-grants-2014_01
ORD IDord-08243579c6024f0b8c3527b5784c60cf
Source noteuspto-grants-2014_01