4-(Dimethylamino)Benzaldehyde → HCID 9887957, compound

HRID 428665Notes

Reaction equation

HRID 428665 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:12])[C:10]#[CH:11])=[CH:5][CH:4]=1.C([Mg]Cl)#C.CN(C)C1C=CC(C=O)=CC=1.Br[C:30]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:31]=1/[C:32](=[CH:40]/[C:41]1[NH:42][CH:43]=[CH:44][C:45]=1[O:46][CH3:47])/[C:33](=[O:39])[NH:34]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>[CH3:13][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:12])[C:10]#[C:11][C:30]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:31]=2/[C:32](=[CH:40]/[C:41]2[NH:42][CH:43]=[CH:44][C:45]=2[O:46][CH3:47])/[C:33](=[O:39])[NH:34]3)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 74794-(Dimethylamino)BenzaldehydeHCID 2749588HCID 2749588, compoundHCID 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 9887957HCID 9887957, 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-dimethylaminophenyl)-3-hydroxy-1-propyne (160 mg, 0.91 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 4-dimethylaminobenzaldehyde (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 (108 mg, 0.34 mmol) (Starting Material 1) using (Ph3P)2PdCl2 (30 mg) (Aldrich) and CuI (16 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 19 h, yielding rac-(Z)-1,3-dihydro-4-[3-(4-dimethylaminophenyl)-3-hydroxy-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 190 mg, 77%).

Sources & evidence

ORD record
ord-8de6509e3f9944e79a8d85397f77d8a9
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

Loading…