Sodium Carbonate → 1h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-

HRID 1172771ノート

反応式

HRID 1172771 の反応式
Br[C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH3:15])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:17]=[CH:16][C:5]3[N:6]([C:15]4[CH:16]=[CH:17][CH:2]=[CH:3][CH:4]=4)[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[N:8][C:4]=3[CH:3]=2)=[CH:21][CH:20]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 230940805-Bromo-1-methyl-2-phenyl-1H-benzo[d]imidazole

生成物 1

HCID 231602311h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-収率 145.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

2.0 g (7.2 mmol) of 5-bromo-1-methyl-2-phenyl-1H-benzimidazole, 1.2 g (7.9 mmol) of 4-chlorophenylboronic acid, and 0.17 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the resultant had been stood to cool, an aqueous layer was removed and an organic layer was dried with magnesium sulfate. After the solvent had been distilled off under reduced pressure, the resultant solid was purified by means of silica gel column chromatography to obtain 2.0 g of 5-(4-chlorophenyl)-1,2-diphenyl-1H-benzimidazole (87% yield).

後処理

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 8 hours in an argon atmosphere
  3. temperatureto cool
  4. customan aqueous layer was removed
  5. dry with materialan organic layer was dried with magnesium sulfate
  6. distillationAfter the solvent had been distilled off under reduced pressure
  7. customthe resultant solid was purified by means of silica gel column chromatography

出典と根拠

ORDレコード
ord-90ff416a5f484d2abe26ef00fa066f79
出典データセット
uspto-grants-2010_11
特許番号
US07833632B2

反応ノート

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