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Water → HCID 9968539, compound

HRID 428723
Notes
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Reaction equation

HRID 428723 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]([N+:26]([O-:28])=[O:27])=[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>[N+: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)([O-:28])=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 962WaterHCID 124951-Iodo-4-nitrobenzeneHCID 9813420HCID 9813420, compound

Product 1

HCID 9968539HCID 9968539, 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 (150 mg, 0.64 mmol) (from Example 82) and 1-iodo-4-nitrobenzene (175 mg, 0.70 mmol) (Aldrich) in N,N-dimethylformamide (3 mL) (Fisher Scientific) and triethylamine (3 mL) was degassed by bubbling argon through the solution for 15 minutes. Copper(I) iodide (13 mg, 0.068 mmol) (Aldrich) and (Ph3P)2PdCl2 (22 mg, 0.031 mmol) (Aldrich) were added, and the reaction mixture was heated at 70° C. for 13 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-nitrophenyl)ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a red powder. (Yield 111 mg, 49%).

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-2ed67f99319f4b419a926cb4961ae414
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