Piperonal → HCID 9909713, compound

HRID 428661Notes

Reaction equation

HRID 428661 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:13])[C:11]#[CH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.C([Mg]Cl)#C.C1C(C=O)=CC2OCOC=2C=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>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:13])[C:11]#[C:12][C:30]3[CH:38]=[CH:37][CH:36]=[C:35]4[C:31]=3/[C:32](=[CH:40]/[C:41]3[NH:42][CH:43]=[CH:44][C:45]=3[O:46][CH3:47])/[C:33](=[O:39])[NH:34]4)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

9

Reactant 4

HCID 8438PiperonalHCID 11789730HCID 11789730, compoundHCID 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 9909713HCID 9909713, 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 D above, 3-(1,3-benzodioxol-5-yl)-3-hydroxy-1-propyne (110 mg, 0.62 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to piperonal (Aldrich) according to Method A above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (100 mg, 0.34 mmol) (Starting Material 1) using (Ph3P)2PdCl2 (30 mg) (Aldrich) and CuI (16 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 16 h, yielding rac-(Z)-4-[3-(1,3-benzodioxol-5-yl)-3-hydroxy-1-propynyl]-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 46 mg, 33%).

Sources & evidence

ORD record
ord-bb53b6c1cf7d4a1cbd9a7db8dbfe4acd
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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