Water → HCID 58175601, compound

HRID 2041828Notes

Reaction equation

HRID 2041828 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[C:6](Br)[C:7]=1[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:24](B(O)O)[CH:25]([CH3:27])[CH3:26].O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C(OCC)(=O)C.ClCCl>[CH2:24]([C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[C:6]([CH2:3][CH:4]([CH3:18])[CH3:5])[C:7]=1[NH:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:25]([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 2734395(2-Methylpropyl)boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 58175700HCID 58175700, compound

Product 1

HCID 58175601HCID 58175601, compoundYield 171.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3,5-dibromobiphenyl-4-yl)benzamide (8.52 g, 19.8 mmol), isobutyl boronic acid (8.06 g, 79.2 mmol), potassium phosphate monohydrate (13.7 g, 59.4 mmol), water. (50 mL) and toluene (150 mL) was purged with nitrogen for 20 min before addition of tris(dibenzylideneacetone) dipalladium(0) (0.27 g 3% Pd) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.49 g, 6 mol %). The reaction was stirred at reflux for 18 h. After cooling to ambient temperature the mixture was diluted with ethyl acetate and water. The layers were separated and the organic layer was concentrated and chromatographed on a silica gel column. Elution first with dichloromethane then dichloromethane and ethyl acetate (49:1) gave 6.53 g (86% yield) of the desired product as a solid. 1H NMR confirmed the structure.

Workup

  1. custom(50 mL) and toluene (150 mL) was purged with nitrogen for 20 min before addition of tris(dibenzylideneacetone) dipalladium(0) (0.27 g 3% Pd) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.49 g, 6 mol %)
  2. temperatureat reflux for 18 h
  3. additionwas diluted with ethyl acetate and water
  4. customThe layers were separated
  5. concentrationthe organic layer was concentrated
  6. customchromatographed on a silica gel column
  7. washElution first with dichloromethane

Sources & evidence

ORD record
ord-3afed11be4664101905e60a609dacfb9
Source dataset
uspto-grants-2013_11
Patent number
US08586204B2

Reaction notes

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