Toluene → HCID 54132950, compound

HRID 1656400Notes

Reaction equation

HRID 1656400 reaction equation
I[C:2]1[N:3]=[C:4]([CH2:9][CH2:10][CH3:11])[NH:5][C:6]=1[CH:7]=[O:8].C1(C)C=CC=CC=1.[C:19]1(B(O)O)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:27]1([C:2]2[N:3]=[C:4]([CH2:9][CH2:10][CH3:11])[NH:5][C:6]=2[CH:7]=[O:8])[C:28]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 178440163HCID 178440163, compound

Product 1

HCID 54132950HCID 54132950, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.64 g (0.01 mol) of 4-iodo-2-n-propylimidazole-5-carboxaldehyde, toluene (40 mL), and 0.33 g (0.00029 mol) of tetrakistriphenylphosphine palladium (0) was stirred at room temperature under nitrogen, while a solution of 3.44 g (0.022 mol) of 1-naphthylboronic acid in 50 mL of ethanol was slowly added. The reaction was stirred for 5 minutes, after which 12 mL of 2M sodium carbonate was slowly added. After the addition was completed, the reaction was refluxed for 48 h and cooled. The reaction was filtered, the filtrate was evaporated under reduced pressure, and the resulting residue was dissolved in 300 mL of methylene chloride, washed twice with 100 mL of saturated sodium chloride solution, washed twice with 100 mL of distilled water, and washed twice with 300 mL of 10% HCl. The HCl layer was made basic with 50% sodium hydroxide until the pH=10. At this point, the basic water layer was extracted three times with 300 mL of methylene chloride, the methylene chloride layer was dried over sodium sulfate and evaporated under reduced pressure. Yield: 0.90 g (0.0034 mol, 34%) of product. NMR (CDCl3) δ 11.45 (m, 1H); 9.42 (s, 1H); 7.28 (m, 7H); 2.82 (t, 2H); 1.85 (m, 2H); 1.01 (t, 3H). ##STR75##

Workup

  1. additionwas slowly added
  2. additionAfter the addition
  3. temperaturethe reaction was refluxed for 48 h
  4. temperaturecooled
  5. filtrationThe reaction was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. dissolutionthe resulting residue was dissolved in 300 mL of methylene chloride
  8. washwashed twice with 100 mL of saturated sodium chloride solution
  9. washwashed twice with 100 mL of distilled water
  10. washwashed twice with 300 mL of 10% HCl
  11. extractionAt this point, the basic water layer was extracted three times with 300 mL of methylene chloride
  12. dry with materialthe methylene chloride layer was dried over sodium sulfate
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-75d13239266d4ebc8f93f8c2a2919121
Source dataset
uspto-grants-1993_10
Patent number
US05254546

Reaction notes

Loading…