2-Methoxybenzaldehyde → HCID 10179099, compound

HRID 428660Notes

Reaction equation

HRID 428660 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[C:3]#[CH:4].C([Mg]Cl)#C.COC1C=CC=CC=1C=O.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:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[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 86582-MethoxybenzaldehydeHCID 109427663-hydroxy-3-(2-methoxyphenyl)-1-propyneHCID 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 10179099HCID 10179099, 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-(2-methoxyphenyl)-1-propyne (150 mg, 0.92 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 2-methoxybenzaldehyde (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) (200 mg, 0.63 mmol) using (Ph3P)2PdCl2 (70 mg) (Aldrich) and CuI (40 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 18 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(2-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yi)methylene]-2H-indol-2-one. (Yield 71 mg, 28%).

Sources & evidence

ORD record
ord-b25f510cea904a2997a7b0c5217fd4ec
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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