Potassium Phosphate, Tribasic → N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamide

HRID 1750918Notes

Reaction equation

HRID 1750918 reaction equation
Br[C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[O:7][C:6]=2[C:5]([NH:15][C:16](=[O:18])[CH3:17])=[C:4](Br)[CH:3]=1.[CH3:20][C:21]1(C)[C:25](C)(C)OB(C(C)=C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:40]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)[CH2:45]CCC[CH2:41]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH2:20]=[C:21]([C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[O:7][C:6]=2[C:5]([NH:15][C:16](=[O:18])[CH3:17])=[C:4]([C:40]([CH3:45])=[CH2:41])[CH:3]=1)[CH3:25]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 58400857N-(1,3-dibromodibenzo[b,d]furan-4-yl)acetamide

Product 1

HCID 58400985N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamideYield 926.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

N-(1,3-dibromodibenzo[b,d]furan-4-yl)acetamide (55 g, 144 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (72.4 g, 431 mmol) and potassium phosphate tribasic (132 g, 574 mmol) were mixed into toluene (800 mL) and water (80 mL). The mixture was bubbled with nitrogen for 20 minutes. Then Pd2(dba)3 (2.63 g, 2.87 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (4.72 g, 11.49 mmol) were added into the reaction mixture. After bubbled by nitrogen for another 20 minutes, the reaction was refluxed overnight under nitrogen. After cooled to room temperature, the organic layer was washed by water, dried over sodium sulfate and concentrated. After silica gel column (30%-50% EtOAc in hexane) got N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamide (32.5 g, 74.1% yield) as brown solid.

Workup

  1. customThe mixture was bubbled with nitrogen for 20 minutes
  2. customAfter bubbled by nitrogen for another 20 minutes
  3. temperaturethe reaction was refluxed overnight under nitrogen
  4. washthe organic layer was washed by water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b0273635c2042969c0ccc953532fd57
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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