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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 366659Generated: October 26, 2026

2-Propynoxyethanol → (Z)-1,3-dihydro-4-[3-(2-hydroxyethoxy)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

https://huagongshe.com/reaction/366659

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-PropynoxyethanolHCID 77596—
Reactant(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 15548053—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
Product(Z)-1,3-dihydro-4-[3-(2-hydroxyethoxy)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 9840790—

Reaction Steps

Using Method C above, 3-(2-hydroxyethoxy)-1-propyne (53 mg, 0.53 mmol) (from Example 21 above) was coupled with (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (150 mg, 0.41 mmol) (Starting Material 2 supra) using (Ph3P)2PdCl2 (20 mg) and Cul (10 mg) as catalyst in DMF (2 mL) and Et3N (2 mL) as solvent at 70° C. for 18 h to yield (Z)-1,3-dihydro-4-[3-(2-hydroxyethoxy)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 68 mg, 49%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06130239
Source datasetuspto-grants-2000_10
ORD IDord-83bdda7be8ab4fd3b47a5e3f576d5559
Source noteuspto-grants-2000_10