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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 366641Generated: October 26, 2026

5-Hexyn-1-ol → (Z)-1,3-dihydro-4-(6-hydroxy-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

https://huagongshe.com/reaction/366641

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Hexyn-1-olHCID 70234—
Reactant(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 18359254—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
Product(Z)-1,3-dihydro-4-(6-hydroxy-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 59959877—

Reaction Steps

Using general Method D above, 5-hexyn-1-ol (56 mg, 0.57 mmol) (Aldrich) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (110 mg, 0.38 mmol) (Starting Material 1 supra) using (Ph3P)2PdCl2 (13 mg) (Aldrich) and Cul (7 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 14 h to yield (Z)-1,3-dihydro-4-(6-hydroxy-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06130239
Source datasetuspto-grants-2000_10
ORD IDord-4282e7b317564828b4ec9c663fbcb4ba
Source noteuspto-grants-2000_10