Phenylacetylene → (Z)-1,3-dihydro-4-(phenylethynyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 428651Notes

Reaction equation

HRID 428651 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1/[C:12](=[CH:20]/[C:21]1[NH:22][CH:23]=[CH:24][CH:25]=1)/[C:13](=[O:19])[NH:14]2>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.CN(C=O)C.CCN(CC)CC>[C:1]1([C:7]#[C:8][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2/[C:12](=[CH:20]/[C:21]2[NH:22][CH:23]=[CH:24][CH:25]=2)/[C:13](=[O:19])[NH:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 2

HCID 10821PhenylacetyleneHCID 59971430(Z)-4-Bromo-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×

Product 1

HCID 59973114(Z)-1,3-dihydro-4-(phenylethynyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Using general Method D above, phenyl acetylene (32 mg, 0.31 mmol) (Aldrich) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 9) (46.3 mg, 0.16 mmol) using (Ph3P)4Pd (8 mg) (Aldrich) and CuI (1.5 mg) (Aldrich) as catalyst in DMF (2 mL) and Et3N (3 mL) as solvent at 85° C. for 18 h, yielding (Z)-1,3-dihydro-4-(phenylethynyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 41 mg, 83%)

Sources & evidence

ORD record
ord-1c91e27a108d4bb79638a9c61863365b
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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