Potassium Carbonate → HCID 86303662, compound

HRID 1476688Notes

Reaction equation

HRID 1476688 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[K+].[K+]>C1(C)C(CO)=CC=CC=1>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 53429652HCID 53429652, compound

Product 1

HCID 86303662HCID 86303662, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 69942-Methylbenzyl alcoholSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-1-phenyl-1H-imidazole (200 mg, 0.9 mmol), furan-2-ylboronic acid (342 mg, 3 mmol), PEPPSI-iPr (18 mg, 0.026 mmol), and K2CO3 (640 mg, 4.64 mmol) were then combined in toluene-methanol (1:1) (4 ml). The reaction mixture was heated under microwave at 80° C. for 20 minutes. It was then filtered and washed with toluene-MeOH (5 ml), and the filtrate was concentrated to yield a crude mixture. The crude mixture was then column purified using 15-20% ethyl acetate/hexanes to afford the desired 4-(furan-2-yl)-1-phenyl-1H-imidazole (50 mg, 0.19 mmol, yield 21.4%) as a brown sticky liquid with an HPLC purity of 95.5%. LC-MS [M+H] 211 (C13H10N2O+H expected 211.08). The 1H-NMR spectra was in accordance with the chemical structure.

Workup

  1. filtrationIt was then filtered
  2. washwashed with toluene-MeOH (5 ml)
  3. concentrationthe filtrate was concentrated
  4. customto yield a crude mixture
  5. customcolumn purified

Sources & evidence

ORD record
ord-61b208f7acdf4b0fa9886a5fa6604814
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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