Iodobenzene → HCID 57860210, compound

HRID 1947149Notes

Reaction equation

HRID 1947149 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].I[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+]>C(O)(C)(C)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:31][CH2:32][N:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:34][CH2:35]1)=[O:28]

Participants

8

Reactant 4

HCID 11575IodobenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 57860479HCID 57860479, compound

Product 1

HCID 57860210HCID 57860210, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of the compound of Example 77 (200 mg, 0.42 mmol), iodobenzene (0.50 mL), tris(dibenzylideneacetone)dipalladium (0) (38 mg, 0.042 mmol), x-phos (40 mg, 0.085 mmol) and sodium tert-butoxide (102 mg, 1.1 mmol) in tert-butanol (4.0 mL) was stirred under microwave irradiation at 130° C. for 35 min. The reaction mixture was diluted with water, and extracted twice with ethyl acetate. The extracts were combined, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=30/70-100/0) and recrystallized from ethyl acetate to give the title compound (70 mg, 30%) as a white solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=30/70-100/0)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d9c2e75b8c044bcfb33748c36807d6df
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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