Dimethylformamide → HCID 58760951, compound

HRID 1766981Notes

Reaction equation

HRID 1766981 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]=1Br)=[O:5])[CH3:2].C([Li])(C)(C)C.CN([CH:34]=[O:35])C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]=1[CH:34]=[O:35])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 57437746HCID 57437746, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 58760951HCID 58760951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (I-2d, 4.4 g, 0.01 mmol) in anhydrous THF (100 ml) at −78° C. was slowly added tert.-butyl lithium (13 ml of 1.7 M solution in pentane, 0.22 mol). After 1 hour, DMF (7.7 ml, 0.1 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 2.5 hours, quenched with sat'd aq. NH4Cl (10 ml), allowed to slowly warm to room temperature, and finally poured into sat'd aq. NaCl. The aqueous solution was extracted with Et2O (3×) and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified via flash chromatography using a solvent gradient of 1:3 EtOAc/hexanes to 1:1 EtOAc/hexanes to give the desired product I-2e as a pale yellow amorphous glass (2.0 g): +APCI MS (M+1) 389.2; 1H NMR (CD2Cl2) δ 1.41 (3H, t), 4.45 (2H, q), 7.09–7.14 (2H, m), 7.24–7.39 (7H, m), 10.50 (1H, s).

Workup

  1. customat −78° C.
  2. customquenched with sat'd aq. NH4Cl (10 ml)
  3. temperatureto slowly warm to room temperature
  4. additionfinally poured into sat'd aq. NaCl
  5. extractionThe aqueous solution was extracted with Et2O (3×)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified via flash chromatography

Sources & evidence

ORD record
ord-58bf18b9312741cc8a969f75134c4413
Source dataset
uspto-grants-2007_06
Patent number
US07232823B2

Reaction notes

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