Water → HCID 67486653, compound

HRID 2371273Notes

Reaction equation

HRID 2371273 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[O:33]1[C:37](B(O)O)=[CH:36][C:35]2[CH:41]=[CH:42][CH:43]=[CH:44][C:34]1=2.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C>[O:33]1[C:34]2=[CH:44][CH:43]=[CH:42][C:41]2=[CH:35][CH:36]=[C:37]1[C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:14][C:12](=[O:13])[CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=1)[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 67486541HCID 67486541, compound

Product 1

HCID 67486653HCID 67486653, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
125 °C

Procedure

To 2-(4-tert-Butyl-phenyl)-N-(4-iodo-phenyl)-3-(4-nitro-phenyl)-propionamide (1056 mg, 2 mmol) in 8 ml 1,2-dimethoxyethane, 4 ml ethanol, and 2 ml water was added benzo[b]furan-2-boronic acid (972 mg, 6 mmol), bis(tri-o-tolylphosphine)palladium(II)dichloride (158 mg, 0.2 mmol), and sodium carbonate (1060 mg, 10 mmol). The reaction mixture was stirred at 125° C. for 6 min, filtered, and concentrated. Chromatography of the residue (20% ethyl acetate in hexane) afforded N-(4-Benzofuran-2-yl-phenyl)-2-(4-tert-butyl-phenyl)-3-(4-nitro-phenyl)-propionamide as a yellow foam (830 mg, 80%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e804f232e4564455bad6d84cf3536cd3
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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