4-Phenoxybenzaldehyde → HCID 9890534, compound

HRID 428666Notes

Reaction equation

HRID 428666 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[C:3]#[CH:4].C([Mg]Cl)#C.O(C1C=CC(C=O)=CC=1)C1C=CC=CC=1.I[C:38]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:39]=1/[C:40](=[CH:48]/[C:49]1[NH:50][CH:51]=[CH:52][C:53]=1[O:54][CH3:55])/[C:41](=[O:47])[NH:42]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]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[C:3]#[C:4][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:39]=1/[C:40](=[CH:48]/[C:49]1[NH:50][CH:51]=[CH:52][C:53]=1[O:54][CH3:55])/[C:41](=[O:47])[NH:42]2

Participants

9

Reactant 4

HCID 661394-PhenoxybenzaldehydeHCID 15548053(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×HCID 18359319HCID 18359319, compoundHCID 178462451HCID 178462451, compound

Product 1

HCID 9890534HCID 9890534, 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-hydroxy-3-(4-phenoxyphenyl)-1-propyne (200 mg, 0.89 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 4-phenoxybenzaldehyde (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, 0.40 mmol) 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)-1,3-dihydro-4-[3-hydroxy-3-(4-phenoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 100 mg, 54%).

Sources & evidence

ORD record
ord-88b12d35e75b49efbef6f69866458d4e
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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