Cesium carbonate → 2-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)benzonitrile

HRID 882201Notes

Reaction equation

HRID 882201 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].I[C:8]1[CH:9]=[CH:10][C:11]2[NH:15][C:14](=[O:16])[N:13]([CH3:17])[C:12]=2[CH:18]=1.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O)#[N:20]>>[CH3:17][N:13]1[C:12]2[CH:18]=[C:8]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:19]#[N:20])[CH:9]=[CH:10][C:11]=2[NH:15][C:14]1=[O:16]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 27346102-Cyanophenylboronic acidHCID 66748876HCID 66748876, compound

Product 1

HCID 667501612-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)benzonitrile

Procedure

A solution of Cesium carbonate (1100 mg, 3.38 mmol, 5.0 eq) was treated with a solution of 6-iodo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (6-3, 185 mg, 0.68 mmol) and 2-Cyanophenylboronic acid (198 mg, 1.35 mmol, 2.0 eq). The 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (27.6 mg, 0.03 mmol, 0.05 eq) was introduced and the mixture was irradiated in a microwave at 140 deg C. for 15 min. The product was worked up by partitioning between EtOAc (2×85 ml) and saturated aqueous NaHCO3 (95 ml), and the combined organic layers were dried over Na2SO4 and concentrated. Afforded 2-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)benzonitrile (6-4), as a maroon-orange solid.

Workup

  1. additionThe 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (27.6 mg, 0.03 mmol, 0.05 eq) was introduced
  2. customthe mixture was irradiated in a microwave at 140 deg C
  3. customby partitioning between EtOAc (2×85 ml) and saturated aqueous NaHCO3 (95 ml)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-361f212c24c0480698433ff3d1cb98a1
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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