2,3-Dimethoxybenzaldehyde → HCID 10224610, compound

HRID 428678Notes

Reaction equation

HRID 428678 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:11]([OH:14])[C:12]#[CH:13].C([Mg]Cl)#C.COC1C(OC)=CC=CC=1C=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[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:11]([OH:14])[C:12]#[C:13][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

Participants

9

Reactant 4

HCID 665812,3-DimethoxybenzaldehydeHCID 14037720HCID 14037720, 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 10224610HCID 10224610, 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-(2,3-dimethoxyphenyl)-3-hydroxy-1-propyne (132 mg, 0.69 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 2,3-dimethoxybenzaldehyde (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 (Starting Material 1) (98 mg, 0.31 mmol) using (Ph3P)2PdCl2 (38 mg) (Aldrich) and CuI (17 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 17 h, yielding rac-(Z)-1,3-dihydro-4-[3-(2,3-dimethoxyphenyl)-3-hydroxy-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 98 mg, 71%).

Sources & evidence

ORD record
ord-acb533db8fb4460c94625b7f86cf8f5f
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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