(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one → (Z)-4-(3-(4-(3-(dimethylamino)propoxy)phenyl)-3-hydroxyprop-1-ynyl)-3-((3-methoxy-1H-pyrrol-2-yl)methylene)indolin-2-one

HRID 428669Notes

Reaction equation

HRID 428669 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([OH:16])[C:14]#[CH:15])=[CH:9][CH:8]=1.I[C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1/[C:21](=[CH:29]/[C:30]1[NH:31][CH:32]=[CH:33][C:34]=1[O:35][CH3:36])/[C:22](=[O:28])[NH:23]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>[CH3:17][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([OH:16])[C:14]#[C:15][C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2/[C:21](=[CH:29]/[C:30]2[NH:31][CH:32]=[CH:33][C:34]=2[O:35][CH3:36])/[C:22](=[O:28])[NH:23]3)=[CH:11][CH:12]=1

Participants

7

Reactant 2

HCID 15548053(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×HCID 183592823-[4-(3-Dimethylaminopropoxy)-phenyl]-3-hydroxy-1-propyne

Product 1

HCID 9890933(Z)-4-(3-(4-(3-(dimethylamino)propoxy)phenyl)-3-hydroxyprop-1-ynyl)-3-((3-methoxy-1H-pyrrol-2-yl)methylene)indolin-2-one

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-[4-(3-dimethylaminopropoxy)-phenyl]-3-hydroxy-1-propyne (201 mg, 0.86 mmol) (from Example 22 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, 0.4 mmol) using (Ph3P)2PdCl2 (34 mg) (Aldrich) and CuI (15 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 16 h, to yield rac-(Z)-1,3-dihydro-4-[3-[4-(3-dimethylaminopropoxy)-phenyl]-3-hydroxy-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 151 mg, 80%).

Sources & evidence

ORD record
ord-3f2ddda150ad40af970cd807ced386ef
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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