Tetraethyl orthocarbonate → HCID 22484970, compound

HRID 1368247Notes

Reaction equation

HRID 1368247 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 by product 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-f4531511e6d441cda40265e3b985a991
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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