5,6-Dimethylbenzimidazole → 2-[4-(5,6-Dimethyl-1H-benzimidazol-1-yl)phenyl}ethyl (4-methylphenyl)sulfonylcarbamate

HRID 724169Notes

Reaction equation

HRID 724169 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:35]([CH3:36])=[CH:34][C:30]2[N:31]=[CH:32][NH:33][C:29]=2[CH:28]=1.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(Cl)Cl>[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:31]3[C:30]4[CH:34]=[C:35]([CH3:36])[C:27]([CH3:26])=[CH:28][C:29]=4[N:33]=[CH:32]3)=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6755,6-DimethylbenzimidazoleHCID 8471TriethylamineHCID 218765304-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acid

Product 1

HCID 213004172-[4-(5,6-Dimethyl-1H-benzimidazol-1-yl)phenyl}ethyl (4-methylphenyl)sulfonylcarbamateYield 22%

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), 5,6-dimethylbenzimidazole (40 mg, 0.28 mmol), Cu(OAc)2 (60 mg, 0.33 mmol), triethylamine (115 μl, 0.83 mmol), MS4A (100 mg), and CH2Cl2 (4 ml) was stirred at room temperature for 1 week. After filtration through a bed of celite, the filtrate was diluted with CH2Cl2, and washed with water. The organic fraction was dried over MgSO4 and filtered. After concentration under reduced pressure, the residue was purified by preparative TLC (CH2Cl2/MeOH=10/1) to afford 28 mg (22%) of the title compound.

Workup

  1. filtrationAfter filtration through a bed of celite
  2. additionthe filtrate was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic fraction was dried over MgSO4
  5. filtrationfiltered
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by preparative TLC (CH2Cl2/MeOH=10/1)

Sources & evidence

ORD record
ord-8b3d909bc9494d0787c1fff36e4418a8
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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