3-Nitrophenylboronic Acid → HCID 15552084, compound

HRID 382017Notes

Reaction equation

HRID 382017 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)/[C:5](=[O:11])[NH:6]2.CCN(CC)CC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[N+:47]([C:50]1[CH:51]=[C:52](B(O)O)[CH:53]=[CH:54][CH:55]=1)([O-:49])=[O:48]>CN(C)C=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[N+:47]([C:50]1[CH:55]=[C:54]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2/[C:4](=[CH:12]/[C:13]2[NH:14][CH:15]=[CH:16][CH:17]=2)/[C:5](=[O:11])[NH:6]3)[CH:53]=[CH:52][CH:51]=1)([O-:49])=[O:48]

Participants

7

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 15552084HCID 15552084, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (35 mg, 0.104 mmol) (Starting Material 1), Et3N (58 μL, 0.415 mmol), tri-o-tolylphosphine (6 mg, 0.020 mmol) (Aldrich), Pd(OAc)2 (2 mg, 0.009 mmol) (Aldrich), and 3-nitrophenylboronic acid (26 mg, 0.156 mmol) (Aldrich) in 3 mL of dry N,N-dimethylformamide was heated at 100° C. for 16 h. The reaction mixture was allowed to cool to room temperature, concentrated in vacuo to remove N,N-dimethylformamide, and then directly purified by flash chromatography (Merck Silica gel 60, 70-230 mesh, 10% ethyl acetate-hexanes then 25% ethyl acetate-hexanes elution) to provide pure (Z)-1,3-dihydro-4-(3-nitrophenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (24.1 mg, 70%) as an orange solid (mp 197-199° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove N,N-dimethylformamide
  3. customdirectly purified by flash chromatography (Merck Silica gel 60, 70-230 mesh, 10% ethyl acetate-hexanes
  4. wash25% ethyl acetate-hexanes elution)

Sources & evidence

ORD record
ord-365681231d5b415bba6b263523eed335
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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