Sodium Bicarbonate → 4-methoxy-2-[1-(4-trifluoromethoxyphenyl)-1H-imidazol-4-yl]-benzaldehyde

HRID 1424714Notes

Reaction equation

HRID 1424714 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[CH:6]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1B(O)O)=[O:19].C(=O)(O)[O-].[Na+].COCCOC.O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1CCCCC1.CCOC(C)=O>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[C:21]([C:2]2[N:3]=[CH:4][N:5]([C:7]3[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=3)[CH:6]=2)[CH:22]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 27343665-Methoxy-2-formylphenylboronic acidHCID 18180031Water 1,2-dimethoxyethaneHCID 578244354-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-imidazole

Product 1

HCID 578244154-methoxy-2-[1-(4-trifluoromethoxyphenyl)-1H-imidazol-4-yl]-benzaldehydeYield 72.8%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-1-(4-trifluoromethoxyphenyl)-1H-imidazole (100 mg, 0.326 mmol), 2-formyl-5-methoxyphenylboronic acid (73 mg, 0.41 mmol), bis(triphenylphosphine)palladium dichloride (2 mg, 0.003 mmol), sodium bicarbonate (49 mg, 0.59 mmol) and 1:1 DME/H2O (8:8 mL) were combined and added to a microwave vessel. The reaction mixture was heated in the microwave with stirring at 100° C. for 12 min. The microwave took 5 min to reach 100° C., then maintained at 100° C. for 12 min, and then cooled. TLC (1:1 EtOAc:cyclohexane) showed the presence of starting materials, thus the sample was heated to 100° C. for another 8 min. Upon cooling a precipitate formed; this was filtered and washed with water to give a grey solid (86 mg): ESIMS m/z 363.0 (M+H).

Workup

  1. additionadded to a microwave vessel
  2. temperatureThe reaction mixture was heated in the microwave
  3. waitThe microwave took 5 min
  4. customto reach 100° C.
  5. temperaturemaintained at 100° C. for 12 min
  6. temperaturecooled
  7. temperaturethus the sample was heated to 100° C. for another 8 min
  8. temperatureUpon cooling a precipitate
  9. customformed
  10. filtrationthis was filtered
  11. washwashed with water

Sources & evidence

ORD record
ord-474f88f0db884f71b3c1379d98719f93
Source dataset
uspto-grants-2015_01
Patent number
US08927729B2

Reaction notes

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