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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1069679Generated: October 29, 2026

1-Octyn-3-ol → rac-(Z)-1,3-dihydro-4-(3-hydroxy-1-octynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

https://huagongshe.com/reaction/1069679

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Octyn-3-olHCID 13166—
Reactant(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 15548053—
CatalystTriphenylphosphineHCID 11776—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
Productrac-(Z)-1,3-dihydro-4-(3-hydroxy-1-octynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 59970994—

Reaction Steps

Using Method C above, rac-1-octyn-3-ol (61 mg, 0.48 mmol) (Aldrich) was coupled with (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (146 mg, 0.4 mmol) (Starting Material 2 supra) using (Ph3P)2PdC[2 (20 mg) and Cul (10 mg) as catalyst in DMF (2 mL) and Et3N (2 mL) as solvent at 70° C. for 15 h to yield rac-(Z)-1,3-dihydro-4-(3-hydroxy-1-octynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 88 mg, 60%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06252086B1
Source datasetuspto-grants-2001_06
ORD IDord-99ea78da98804a31bf8b1504da9b6af6
Source noteuspto-grants-2001_06