Benzimidazole → 1-(1H-Inden-2-yl)-1H-benzimidazole

HRID 1178690Notes

Reaction equation

HRID 1178690 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1B(O)O.[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 5798BenzimidazoleHCID 109427391H-INDENE-2-BORONIC ACID

Product 1

HCID 64256251-(1H-Inden-2-yl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml Erlenmeyer flask a mixture of 3.20 g (20.0 mmol) of 1H-inden-2-ylboronic acid, 1.18 g (10.0 mmol) of benzimidazole, 0.93 g (2.00 mmol) of [(TMEDA)CuOH]2Cl2, and 40 ml of dichloromethane was stirred for 20 hours (in air). The resulted mixture was passed through short column with Silica Gel 60 (40-63 μm, d 40 mm, l 20 mm). This column was additionally washed by 500 ml of dichloromethane. The combined elute was evaporated to dryness. The crude product was purified using medium-pressure chromatography on Silica Gel 60 (40-63 μm, d 40 mm, l 350 mm; eluent: hexanes/dichloromethane=1/1). Yield 530 mg (23%) of white solid.

Workup

  1. washThis column was additionally washed by 500 ml of dichloromethane
  2. washThe combined elute
  3. customwas evaporated to dryness
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-60bc68fbb3cb4a478b54757f285dbd12
Source dataset
uspto-grants-2007_10
Patent number
US07276567B2

Reaction notes

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