Pyridine → HCID 53429652, compound

HRID 1476687Notes

Reaction equation

HRID 1476687 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CC=CC=1>ClCCl>[Br: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 1049PyridineHCID 66827Phenylboronic AcidHCID 178418934HCID 178418934, compound

Product 1

HCID 53429652HCID 53429652, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-1H-imidazole (500 mg, 3.4 mmol, 1 eq), phenylboronic acid (830 mg, 6.8 mmol, 2 eq), anhydrous cupric acetate (926 mg, 5.1 mmol), activated 4 Å molecular sieves (2 g) and pyridine (0.3 ml) were combined in dichloromethane (20 ml) and stirred for 2 days in the presence of air. The reaction mass was then filtered through Celite, washed with methanol, and concentrated and purified by silica gel chromatography (eluent 15% ethyl acetate/hexane) to afforded yellowish sticky solid 4-bromo-1-phenyl-1H-imidazole (200 mg, 26%).

Workup

  1. filtrationThe reaction mass was then filtered through Celite
  2. washwashed with methanol
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (eluent 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-63adece0322141ebb8092ff18f18fc28
Source dataset
uspto-grants-2016_08
Patent number
US09402397B2

Reaction notes

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