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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1069687Generated: October 28, 2026

Propargyl alcohol → (Z)-1,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

https://huagongshe.com/reaction/1069687

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPropargyl alcoholHCID 7859—
Reactant(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-oneHCID 18366067—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
Product(Z)-1,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-oneHCID 9949778—

Reaction Steps

Using Method C above, propargyl alcohol (0.11 g, 1.95 mmol) (Aldrich) was coupled with (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (0.32 g, 0.78 mmol) (Starting Material 2 above) using (Ph3P)2PdCl2 (27.4 mg) and Cul (7.4 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 85° C. for 18 h to yield (Z)-1,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one. (Yield 0.12 g, 46%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06252086B1
Source datasetuspto-grants-2001_06
ORD IDord-4c679b31ee0c4e0dad6f58fcbee6fbb7
Source noteuspto-grants-2001_06