Pyridine → HCID 54554517, compound

HRID 1867550Notes

Reaction equation

HRID 1867550 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[C:12]1([C:18]2[N:19]=[CH:20][NH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.N1C=CC=CC=1>CN(C)C=O.ClCCl.N.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[C:12]1([C:18]2[N:19]=[CH:20][N:21]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=3)[CH:22]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 178418822HCID 178418822, compound

Product 1

HCID 54554517HCID 54554517, compoundYield 72.7%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 222AmmoniaSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3.04 g (20 mmol) of 4-(hydroxymethyl)phenylboronic acid, 1.44 g (10 mmol) of 4-phenylimidazole, 2.8 ml (20 mmol) of triethylamine and 1.64 ml (20 mmol) of pyridine are dissolved in 20 ml of dimethylformamide. 2.72 g (15 mmol) of copper diacetate are added and the mixture is stirred for 24 hours at ambient temperature. It is diluted with 200 ml of dichloromethane and 200 ml of aqueous 28% ammonia solution. After the phases have settled and been separated, the aqueous phase is extracted with 100 ml of dichloromethane. The organic phases are washed with 50 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 97/3 then 95/5 mixture of dichloromethane and methanol. The product is recrystallized from a mixture of toluene and diisopropyl ether, to give 1.82 g of product in the form of white crystals.

Workup

  1. custombeen separated
  2. extractionthe aqueous phase is extracted with 100 ml of dichloromethane
  3. washThe organic phases are washed with 50 ml of saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. customThe product is purified by chromatography on silica gel
  7. washeluting with a 97/3
  8. addition95/5 mixture of dichloromethane and methanol
  9. customThe product is recrystallized from a mixture of toluene and diisopropyl ether

Sources & evidence

ORD record
ord-addbcc95d9ff4249af7edf730275f29c
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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