3-Thiophenecarboxaldehyde → HCID 9885990, compound

HRID 428675Notes

Reaction equation

HRID 428675 reaction equation
[OH:1][CH:2]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)[C:3]#[CH:4].C([Mg]Cl)#C.S1C=CC(C=O)=C1.Br[C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1/[C:24](=[CH:32]/[C:33]1[NH:34][CH:35]=[CH:36][C:37]=1[O:38][CH3:39])/[C:25](=[O:31])[NH:26]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:1][CH:2]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)[C:3]#[C:4][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1/[C:24](=[CH:32]/[C:33]1[NH:34][CH:35]=[CH:36][C:37]=1[O:38][CH3:39])/[C:25](=[O:31])[NH:26]2

Participants

9

Reactant 4

HCID 681353-ThiophenecarboxaldehydeHCID 11205786HCID 11205786, 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 9885990HCID 9885990, 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-hydroxy-3-(thiophen-3-yl)-1-propyne (131 mg, 0.95 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 3-thiophenecarboxaldehyde (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 (107 mg, 0.34 mmol) (Starting Material 1) using (Ph3P)2PdCl2 (32 mg) (Aldrich) and CuI (17 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. or 18 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(thiophen-3-yl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 93 mg, 72%).

Sources & evidence

ORD record
ord-f2db1fa430754f1f9233cb161ef77410
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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