Vanillin → rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 428662Notes

Reaction equation

HRID 428662 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1)[C:3]#[CH:4].C([Mg]Cl)#C.O=CC1C=CC(O)=C(OC)C=1.Br[C:30]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:31]=1/[C:32](=[CH:40]/[C:41]1[NH:42][CH:43]=[CH:44][C:45]=1[O:46][CH3:47])/[C:33](=[O:39])[NH:34]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>[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1)[C:3]#[C:4][C:30]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:31]=1/[C:32](=[CH:40]/[C:41]1[NH:42][CH:43]=[CH:44][C:45]=1[O:46][CH3:47])/[C:33](=[O:39])[NH:34]2

Participants

9

Reactant 4

HCID 1183VanillinHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×HCID 183592563-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propyneHCID 178462451HCID 178462451, compound

Product 1

HCID 9801994rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

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 D above, 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propyne (197 mg, 1.1 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to vanillin (Aldrich) according to Method B above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 1) (116 mg, 0.36 mmol) using (Ph3P)2PdCl2 (33 mg) (Aldrich) and CuI (18 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 16 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 31 mg, 21%).

Sources & evidence

ORD record
ord-38a094e9c37e433f91a2ba6b1936512e
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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