1-(4-Methoxyphenyl)prop-2-yn-1-ol → HCID 9887224, compound

HRID 428655Notes

Reaction equation

HRID 428655 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:3]#[CH:4].C([Mg]Cl)C.COC1C=CC(C=O)=CC=1.Br[C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1/[C:30](=[CH:38]/[C:39]1[NH:40][CH:41]=[CH:42][C:43]=1[O:44][CH3:45])/[C:31](=[O:37])[NH:32]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:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:3]#[C:4][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1/[C:30](=[CH:38]/[C:39]1[NH:40][CH:41]=[CH:42][C:43]=1[O:44][CH3:45])/[C:31](=[O:37])[NH:32]2

Participants

9

Reactant 4

HCID 294331-(4-Methoxyphenyl)prop-2-yn-1-olHCID 312444-MethoxybenzaldehydeHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×HCID 178461633HCID 178461633, compound

Product 1

HCID 9887224HCID 9887224, 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-hydroxy-3-(4-methoxyphenyl)-1-propyne (115 mg, 0.70 mmol) (prepared by the addition of ethylmagnesium chloride (Aldrich) to 4-methoxybenzaldehyde (Aldrich) according to Method A above), was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 1) (174 mg, 0.55 mmol) using (Ph3P)2PdCl2 (18 mg) (Aldrich) and CuI (10 mg) (Aldrich) as catalyst in DMF (2.5 mL) and Et3N (2.5 mL) as solvent at 70° C. for 15 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 32 mg, 32%).

Sources & evidence

ORD record
ord-24a2eb86d71d45108b6d5cf27c3cae0a
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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