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Water → HCID 9923369, compound

HRID 428718
Notes
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Reaction equation

HRID 428718 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])/[C:6]/2=[CH:13]\[C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1)#[CH:2].I[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.O>CN(C)C=O.C(N(CC)CC)C.[Cu]I.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>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])/[C:6]/3=[CH:13]\[C:14]2[NH:15][CH:16]=[CH:17][CH:18]=2)=[CH:21][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 962WaterHCID 108944-IodophenolHCID 9813420HCID 9813420, compound

Product 1

HCID 9923369HCID 9923369, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (Z)-1,3-dihydro-5-ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (100 mg, 0.43 mmol) (from Example 82) and 4-iodophenol (104 mg, 0.47 mmol) (Aldrich) in N,N-dimethylformamide (2 mL) and triethylamine (2 mL) was degassed by bubbling argon through the solution for 15 minutes. Copper(I) iodide (8 mg, 0.042 mmol) (Aldrich) and (Ph3P)2PdCl2 (25 mg, 0.021 mmol) (Aldrich) were added, and the reaction was heated at 70° C. for 16 hours. Water (15 mL) was then added and the precipitate was filtered off and dried. The product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane to give (Z)-1,3-dihydro-5-(4-hydroxyphenyl)ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a yellow powder. (Yield 121 mg, 86%).

Workup

  1. customby bubbling argon through the solution for 15 minutes
  2. filtrationthe precipitate was filtered off
  3. customdried
  4. customThe product was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane

Sources & evidence

ORD record
ord-41afd9451b19465db102f418896de19a
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06313310B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes