3-Methyl-1-hexyn-3-ol → rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-methyl-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 380821Notes

Reaction equation

HRID 380821 reaction equation
[CH3:1][C:2]([OH:8])([CH2:5][CH2:6][CH3:7])[C:3]#[CH:4].[Na+].[CH3:10][O:11][C:12]1[CH:16]=[CH:15][NH:14][C:13]=1/[CH:17]=[C:18]1\[C:19](=[O:34])[NH:20][C:21]2[C:26]\1=[C:25](C#CCCC([O-])=O)[CH:24]=[CH:23][CH:22]=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:8][C:2]([CH3:1])([CH2:5][CH2:6][CH3:7])[C:3]#[C:4][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:26]=1/[C:18](=[CH:17]/[C:13]1[NH:14][CH:15]=[CH:16][C:12]=1[O:11][CH3:10])/[C:19](=[O:34])[NH:20]2

Participants

7

Reactant 2

HCID 203473-Methyl-1-hexyn-3-olHCID 23683387HCID 23683387, compound2×

Product 1

HCID 9884773rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-methyl-1-hexynyl)-3-[(3-methoxy-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 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Using Method D above, 3-methyl-1-hexyn-3-ol (98 mg, 0.87 mmol) (Aldrich) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material I supra) (127 mg, 0.4 mmol) using (Ph3P)2PdCl2 (46 mg) and CuI (22 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 22 h yielding rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-methyl-1-hexynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 92 mg, 66%).

Sources & evidence

ORD record
ord-473317c3165c4675a0b1426ebcddaee8
Source dataset
uspto-grants-2001_10
Patent number
US06303793B1

Reaction notes

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