Veratraldehyde → HCID 10296318, compound

Participants

Role	Name	HCID	Charge
Reactant	Veratraldehyde	HCID 8419	—
Reactant	α-Ethynyl-3,4-dimethoxybenzenemethanol	HCID 236412	—
Reactant	(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one	HCID 18359254	—
Reactant	HCID 178462451	HCID 178462451	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Triethylamine	HCID 8471	—
Product	HCID 10296318	HCID 10296318	—

Reaction Steps

Using Method C above, 3-(3,4-dimethoxyphenyl)-3-hydroxy-1-propyne (150 mg, 0.78 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 3,4-dimethoxybenzaldehyde (Aldrich) according to Method A above) was coupled to (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 2) (146 mg, 0.4 mmol) using (Ph3P)2PdCl2 (40 mg) (Aldrich) and CuI (22 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 18 h, yielding rac-(Z)-1,3-dihydro-4-[3-(3,4-dimethoxyphenyl)-3-hydroxy-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 121 mg, 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06313310B1
Source dataset	uspto-grants-2001_11
ORD ID	ord-c9dd28fc4e424aa29b151c1307b6464a
Source note	uspto-grants-2001_11