Veratraldehyde → HCID 10296318, compound

HRID 428679Notes

Reaction equation

HRID 428679 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:14])[C:12]#[CH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Mg]Cl)#C.COC1C=C(C=CC=1OC)C=O.Br[C:32]1[CH:40]=[CH:39][CH:38]=[C:37]2[C:33]=1/[C:34](=[CH:42]/[C:43]1[NH:44][CH:45]=[CH:46][C:47]=1[O:48][CH3:49])/[C:35](=[O:41])[NH:36]2>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CN(C=O)C.CCN(CC)CC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:14])[C:12]#[C:13][C:32]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:33]=2/[C:34](=[CH:42]/[C:43]2[NH:44][CH:45]=[CH:46][C:47]=2[O:48][CH3:49])/[C:35](=[O:41])[NH:36]3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

9

Reactant 4

HCID 8419VeratraldehydeHCID 236412α-Ethynyl-3,4-dimethoxybenzenemethanolHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×HCID 178462451HCID 178462451, compound

Product 1

HCID 10296318HCID 10296318, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

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%).

Sources & evidence

ORD record
ord-c9dd28fc4e424aa29b151c1307b6464a
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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