Sodium Carbonate → 2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-phenyl-1H-benzoimidazole

HRID 1661893Notes

Reaction equation

HRID 1661893 reaction equation
Br[C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:17]([C:14]1[CH:13]=[CH:12][C:11]([C:8]2[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]3[C:5]([O:24][CH3:25])=[CH:4][CH:3]=[C:2]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:10]=3[N:9]=2)=[CH:16][CH:15]=1)([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 112811194-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

Product 1

HCID 113041412-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-phenyl-1H-benzoimidazoleYield 52.9%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 22272177Toluene waterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 100 mg (0.25 mmol) 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole, 45 mg (0.424 mmol) sodium carbonate, 34 mg (0.275 mmol) phenyl-boronic acid and 10 mg tetrakis(triphenylphosphine) palladium in 10 ml toluene/water (3:1) is stirred at 100° C. for 9 hours. Then the reaction mixture is cooled to room temperature and poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=4:1) to afford 53 mg of the title compound as a white crystalline solid.

Workup

  1. temperatureThen the reaction mixture is cooled to room temperature
  2. additionpoured on water
  3. extractionextracted (3×) with ethyl acetate
  4. washThe combined organic layers are washed with water (2×) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=4:1)

Sources & evidence

ORD record
ord-bf4e411e598b4474b95936e92401b1a0
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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