Triethylamine → 2-[4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate

HRID 891170Notes

Reaction equation

HRID 891170 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.[CH3:26][C:27]1[C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:30][NH:29][N:28]=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:29]3[CH:30]=[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:27]([CH3:26])=[N:28]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 178434528HCID 178434528, compound

Product 1

HCID 865909252-[4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl (4-methylphenyl)sulfonylcarbamateYield 21.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)oxy]ethyl}phenylboronic acid (200 mg, 0.55 mmol), 3-methyl-4-phenylpyrazole (87 mg, 0.55 mmol), Copper(II) acetate (120 mg, 0.66 mmol), triethylamine (0.23 mL, 1.65 mmol), molecular sieves 4A (200 mg), and dichloromethane (8 mL) was stirred at room temperature for 3 days. After filtration through a bed of celite, the filtrate was diluted with dichloromethane, and washed with water. The organic fraction was dried over MgSO4. After concentration under reduced pressure, the residue was purified by TLC with dichloromethane/ethylacetate (10:1) to afford 56 mg (21%) of the title compound as white solids: MS (ESI) m/z 476 [M+H]+, 474 [M−H]−, 1H-NMR (CDCl3) δ 7.88 (2H, d, J=8.5 Hz), 7.61-7.19 (11H, m), 4.31 (2H, t, J=6.6 Hz), 2.92 (2H, t, J=6.6 Hz), 2.49 (3H, s), 2.42 (3H, s).

Workup

  1. filtrationAfter filtration through a bed of celite
  2. additionthe filtrate was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic fraction was dried over MgSO4
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was purified by TLC with dichloromethane/ethylacetate (10:1)

Sources & evidence

ORD record
ord-fcbaa978d9b44a4a864d71193b8f3553
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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