4-Formylbenzoic acid → HCID 9932323, compound

HRID 428658Notes

Reaction equation

HRID 428658 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:13])[C:11]#[CH:12])=[CH:6][CH:5]=1.C([Mg]Cl)#C.C(C1C=CC(C=O)=CC=1)(O)=O.Br[C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1/[C:33](=[CH:41]/[C:42]1[NH:43][CH:44]=[CH:45][C:46]=1[O:47][CH3:48])/[C:34](=[O:40])[NH:35]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>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:13])[C:11]#[C:12][C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2/[C:33](=[CH:41]/[C:42]2[NH:43][CH:44]=[CH:45][C:46]=2[O:47][CH3:48])/[C:34](=[O:40])[NH:35]3)=[CH:6][CH:5]=1

Participants

9

Reactant 4

HCID 120884-Formylbenzoic acidHCID 10583822HCID 10583822, 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 9932323HCID 9932323, 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, 4-(1-hydroxy-2-propynyl)-benzoic acid methyl ester (137 mg, 0.72 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 4-carboxybenzaldehyde (Aldrich) using Method B above to give the acid which was converted to its methyl ester by Method E 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) (221 mg, 0.69 mmol) using (Ph3P)2PdCl2 (37 mg) (Aldrich) and CuI (18 mg) (Aldrich) as catalyst in DMF (4 mL) and Et3N (4 mL) as solvent at 70° C. for 18 h, yielding rac-(Z)-4-[3-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-1-hydroxy-2-propynyl]benzoic acid methyl ester. (Yield 52 mg, 18%).

Workup

  1. customto give the acid which

Sources & evidence

ORD record
ord-b853b5179a9a4084b1815c4e6db1776f
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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