Tetraethyl orthocarbonate → HCID 22484970, compound

HRID 2181039Notes

Reaction equation

HRID 2181039 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][C:12]=2[Cl:23])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1.[CH2:24]([O:26][C:27](OCC)(OCC)OCC)[CH3:25]>C(O)(=O)C>[Br:8][C:5]1[N:4]=[C:3]2[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:13][C:12]=3[Cl:23])[C:27]([O:26][CH2:24][CH3:25])=[N:1][C:2]2=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 66213Tetraethyl orthocarbonateHCID 22484980HCID 22484980, compound

Product 1

HCID 22484970HCID 22484970, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-amino-6-bromo-2-(N-(2-chloro-4-phenylbenzyl)amino)pyridine (1.85 g), tetraethoxymethane (4.3 g) and acetic acid (18.5 ml) was stirred at room temperature overnight and at 70° C. for 7 hr. The reaction mixture was concentrated to dryness under reduced pressure, and toluene was added, which was followed by concentration under reduced pressure. The residue was dissolved in ethyl acetate and washed twice with saturated aqueous sodium hydrogen carbonate solution and once with saturated brine. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was applied to silica gel column (n-hexane:ethyl acetate=9:1) to give a single product (55 mg) of 5-bromo-3-(2-chloro-4-phenylbenzyl)-2-ethoxy-3H-imidazo[4,5-b]pyridine and a mixture (977 mg) with a byproduct each as pale-brown amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure, and toluene
  2. additionwas added
  3. concentrationwhich was followed by concentration under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed twice with saturated aqueous sodium hydrogen carbonate solution and once with saturated brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-747b2d97aa344c16a5cad9bd3f37da6f
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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