1,1'-Carbonyldiimidazole → 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1255865Notes

Reaction equation

HRID 1255865 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)=[CH:7][C:5]=1[NH2:6])([O-])=O.C1N=CN([C:25](N2C=NC=C2)=[O:26])C=1>C(OCC)(=O)C.C(Cl)Cl.[Pt](=O)=O>[CH3:18][C:13]1([CH3:19])[C:14]([CH3:17])([CH3:16])[O:15][B:11]([C:8]2[CH:9]=[CH:10][C:4]3[NH:1][C:25](=[O:26])[NH:6][C:5]=3[CH:7]=2)[O:12]1

Participants

6

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 597369762-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.35 g, 8.9 mmol) in ethyl acetate (100 mL) was treated with platinum(IV) oxide (0.2 g) and stirred vigorously under a hydrogen atmosphere for 30 minutes. The reaction mixture was degassed with nitrogen and filtered through celite washing with ethyl acetate. This solution was then treated with CDI (1.8 g, 11.1 mmol) and stirred overnight at ambient temperature. The solution was diluted with methylene chloride (100 mL) and the precipate was filtered and washed with cold methanol. The solids were dried in vacuo to yield 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzimidazol-2-one as a white solid.

Workup

  1. customThe reaction mixture was degassed with nitrogen
  2. filtrationfiltered
  3. washthrough celite washing with ethyl acetate
  4. stirringstirred overnight at ambient temperature
  5. filtrationthe precipate was filtered
  6. washwashed with cold methanol
  7. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-90484b7f86ca431fa68edd93eee71d77
Source dataset
uspto-grants-2013_06
Patent number
US08461162B2

Reaction notes

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