2-Thiophenecarboxaldehyde → HCID 9969774, compound

HRID 428684Notes

Reaction equation

HRID 428684 reaction equation
[OH:1][CH:2]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[C:3]#[CH:4].C([Mg]Cl)#C.S1C=CC=C1C=O.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[S:6][CH:7]=[CH:8][CH:9]=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 73642-ThiophenecarboxaldehydeHCID 130127143-Hydroxy-3-(2-thiophenyl)-1-propyneHCID 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 9969774HCID 9969774, 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-(2-thiophenyl)-1-propyne (102 mg, 0.74 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 2-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 (126 mg, 0.39 mmol) (Starting Material 1) using (Ph3P)2PdCl2 (35 mg) (Aldrich) and CuI (17 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 18 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(2-thiophenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 105 mg, 71%).

Sources & evidence

ORD record
ord-8a15fa2a8113437790828d14f4cb533c
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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