Triethylamine → (Z)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-4-(2-thiophenyl)-2H-indol-2-one

HRID 382014Notes

Reaction equation

HRID 382014 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.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1B(O)O>CN(C)C=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[NH:14]1[CH:15]=[CH:16][CH:17]=[C:13]1/[CH:12]=[C:4]1\[C:5](=[O:11])[NH:6][C:7]2[C:3]\1=[C:2]([C:26]1[S:25][CH:29]=[CH:28][CH:27]=1)[CH:10]=[CH:9][CH:8]=2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27339602-Thiopheneboronic acidHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 9948007(Z)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-4-(2-thiophenyl)-2H-indol-2-oneYield 83.3%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (36.9 mg, 0.110 mmol) (Starting Material 1), Et3N (46 μL, 0.329 mmol), tri-o-tolylphosphine (2.1 mg, 0.007 mmol) (Aldrich), Pd(OAc)2 (0.7 mg, 0.003 mmol) (Aldrich), and 2-thiopheneboronic acid (21.1 mg, 0.165 mmol) (Aldrich) in 439 μL of dry N,N-dimethylformamide was heated at 100° C. for 24 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-3-[(1H-pyrrol-2-yl)methylene]-4-(2-thiophenyl)-2H-indol-2-one (Yield 26.8 mg, 83%) as an orange solid (mp 213-214° 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-261c5bc74ba24d5196b0bde85f19ca82
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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