3-Hydroxybenzaldehyde → HCID 10156965, compound

HRID 428656Notes

Reaction equation

HRID 428656 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[C:3]#[CH:4].C([Mg]Cl)#C.OC1C=C(C=CC=1)C=O.Br[C:26]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:27]=1/[C:28](=[CH:36]/[C:37]1[NH:38][CH:39]=[CH:40][C:41]=1[O:42][CH3:43])/[C:29](=[O:35])[NH:30]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:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[C:3]#[C:4][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:27]=1/[C:28](=[CH:36]/[C:37]1[NH:38][CH:39]=[CH:40][C:41]=1[O:42][CH3:43])/[C:29](=[O:35])[NH:30]2

Participants

9

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×HCID 18359312HCID 18359312, compoundHCID 178462451HCID 178462451, compound

Product 1

HCID 10156965HCID 10156965, 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-(3-hydroxyphenyl)-1-propyne (140 mg, 0.94 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 3-hydroxybenzaldehyde (Aldrich) through Method B above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 1) (200 mg, 0.63 mmol) using (Ph3P)2PdCl2 (68 mg) (Aldrich) and CuI (32 mg) (Aldrich) as catalyst in DMF (4 mL) and Et3N (4 mL) as solvent at 80° C. for 15 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(3-hydroxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 82 mg, 31%).

Sources & evidence

ORD record
ord-897fa9c0dfa94ad8ae5151bf541fae96
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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