Triethylamine → 2-[4-(4-Phenyl-1H-imidazole-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate

HRID 967807Notes

Reaction equation

HRID 967807 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:26]1([C:32]2[N:33]=[CH:34][NH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:13])[O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:35]3[CH:36]=[C:32]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:33]=[CH:34]3)=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 218765304-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acidHCID 178418822HCID 178418822, compound

Product 1

HCID 98471322-[4-(4-Phenyl-1H-imidazole-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamateYield 46%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-{2-[({[(4-Methylphenyl)sulfonyl]amino}carbonyl)oxy]ethyl}phenylboronic acid (100 mg, 0.28 mmol), 4-phenylimidazole (40 mg, 0.28 mmol), Copper(II) acetate (50 mg, 0.28 mmol), triethylamine (115 μL, 0.83 mmol), molecular sieves 4A (100 mg), and dichloromethane (4 mL) was stirred at room temperature for 1 week. Insoluble materials were removed by Celite pad, the filtrate was diluted with dichloromethane, and washed with water. The combined organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by TLC with dichloromethane/methanol (10:1) to afford 58 mg (46%) of the title compound as white solids: MS (ESI) m/z 462 [M+H]+, 460 [M−H]−, 1H-NMR (DMSO-d6) δ 2.35 (3H, s), 2.88 (2H, t, J=6.5 Hz), 4.23 (2H, t, J=6.5 Hz), 7.22-7.43 (7H, m), 7.62 (2H, d, J=8.3 Hz), 7.74 (2H, d, J=8.3 Hz), 7.86 (2H, d, J=7.3 Hz), 8.26 (1H, s), 8.32 (1H, s).

Workup

  1. customInsoluble materials were removed by Celite pad
  2. additionthe filtrate was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by TLC with dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-0e24fd68fde4490bb26a2095943084cf
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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