Sodium Carbonate → HCID 68814364, compound

HRID 732575Notes

Reaction equation

HRID 732575 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16]([O:23][C:24](=[O:39])[C:25]1[CH:37]=[C:36](I)[CH:35]=[C:27]([C:28]([N:30]([CH3:34])[CH2:31][CH2:32][CH3:33])=[O:29])[CH:26]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>COCCOC.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]>[CH2:16]([O:23][C:24](=[O:39])[C:25]1[CH:37]=[C:36]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:35]=[C:27]([C:28]([N:30]([CH3:34])[CH2:31][CH2:32][CH3:33])=[O:29])[CH:26]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 68814398HCID 68814398, compound

Product 1

HCID 68814364HCID 68814364, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Add pyridine-4-boronic acid (2.361 g, 19.21 mmol) and 2 N sodium carbonate (19.21 mL, 38.42 mmol) to a solution of 5-iodo-N-methyl-N-propyl-isophthalamic acid benzyl ester (6.000 g, 13.72 mmol)in ethylene glycol dimethyl ether (206 mL) under nitrogen at room temperature. Add tetrakis(triphenylphosphine)palladium (0) (0.634 g, 0.549 mmol) and reflux for 20 h. Cool to room temperature and concentrate. Add ethyl acetate, separate the organic layer and extract the aqueous layer with ethyl acetate (4×). Wash the combined organic layers with H2O, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate) to give the title compound (56%).

Workup

  1. concentrationconcentrate
  2. customAdd ethyl acetate, separate the organic layer
  3. extractionextract the aqueous layer with ethyl acetate (4×)
  4. washWash the combined organic layers with H2O, saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-809a3f122f5741d2a3dc412d8a857ac0
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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