HCID 18359252, compound → HCID 10299508, compound

HRID 428697Notes

Reaction equation

HRID 428697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:11])[C:9]#[CH:10])=[C:4]([O:12][CH2:13][S:14][CH3:15])[CH:3]=1.Br[C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1/[C:19](=[CH:27]/[C:28]1[NH:29][CH:30]=[CH:31][C:32]=1[O:33][CH3:34])/[C:20](=[O:26])[NH:21]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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:11])[C:9]#[C:10][C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2/[C:19](=[CH:27]/[C:28]2[NH:29][CH:30]=[CH:31][C:32]=2[O:33][CH3:34])/[C:20](=[O:26])[NH:21]3)=[C:4]([O:12][CH2:13][S:14][CH3:15])[CH:3]=1

Participants

7

Reactant 2

HCID 18359252HCID 18359252, compoundHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×

Product 1

HCID 10299508HCID 10299508, 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-(4-chloro-2-methylsulfanylmethoxy-phenyl)-3-hydroxy-1-propyne (158 mg, 0.65 mmol) (from Example 53 above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (152 mg, 0.48 mmol) (Starting Material 1) using (Ph3P)2PdCl2 (40 mg) (Aldrich) and CuI (22 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 17 h, yielding rac-(Z)-4-[3-(4-chloro-2-methylsulfanylmethoxy-phenyl)-3-hydroxy-1-propynyl]-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 132 mg, 57%).

Sources & evidence

ORD record
ord-59360382df884064b51ef19757e62576
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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