Ammonium Chloride → methyl 4-[(E)-3-(1-tritylimidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

HRID 1019043Notes

Reaction equation

HRID 1019043 reaction equation
C([Mg]Br)C.[C:5]([N:24]1[C:28](I)=[CH:27][N:26]=[CH:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cu]C#N.[Cl-].[Li+].Br[CH2:36][CH:37]=[CH:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[C:41]([C:49]2[CH:54]=[CH:53][C:52]([F:55])=[CH:51][CH:50]=2)[CH:40]=1.[Cl-].[NH4+]>C1COCC1>[C:5]([N:24]1[C:28]([CH2:36]/[CH:37]=[CH:38]/[C:39]2[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[C:41]([C:49]3[CH:50]=[CH:51][C:52]([F:55])=[CH:53][CH:54]=3)[CH:40]=2)=[CH:27][N:26]=[CH:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 6

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 154285835-iodo-1-trityl-1H-imidazoleHCID 54112501Methyl 2-(4-fluorophenyl)-4-(3-bromoprop-1-en-1-yl)benzoateHCID 178418443HCID 178418443, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 18399521methyl 4-[(E)-3-(1-tritylimidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl magnesium bromide (3M solution in ether; 5.7 ml; 17 mmol) was added dropwise at 0° C. under argon atmosphere to a solution of N-trityl 5-iodoimidazole (6.1 g; 14 mmol). After stirring at 0° C. for 1 hour, a solution of copper (I) cyanide (0.27 g; 3 mmol) and lithium chloride (0.252 g; 6 mmol) in THF (5 ml) was added. The mixture was cooled down to −78° C. and a solution of methyl 4-(3-bromoprop-1-en-1-yl)-2-(4-fluorophenyl)benzoate (3.5 g; 10 mmol) in THF (10 ml) was added. After stirring at −78° C. for 15 minutes, the temperature was allowed to raise to room temperature. The mixture was stirred further overnight. After addition of aqueous ammonium chloride solution and evaporation to dryness, the residue was extracted with dichloromethane/distilled water. The organic layer was evaporated to give methyl 4-[(E)-3-(1-tritylimidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was cooled down to −78° C.
  2. stirringAfter stirring at −78° C. for 15 minutes
  3. temperatureto raise to room temperature
  4. stirringThe mixture was stirred further overnight
  5. extractionthe residue was extracted with dichloromethane/
  6. distillationdistilled water
  7. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-51ad9ecd638e4dd8b70f435f8d04fd10
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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