Water → 5-(2-aminophenyl)-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile

HRID 1920264ノート

反応式

HRID 1920264 の反応式
O.C(=O)([O-])[O-].[Na+].[Na+].I[C:9]1[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:12]([CH2:18][CH2:19][CH3:20])=[N:11][C:10]=1[C:21]#[N:22].Cl.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)CC>[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:9]1[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:12]([CH2:18][CH2:19][CH3:20])=[N:11][C:10]=1[C:21]#[N:22]

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 164270902-Aminophenylboronic acid hydrochlorideHCID 585001345-iodo-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile

生成物 1

HCID 585001375-(2-aminophenyl)-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile収率 119.2%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 10311-Propanol溶媒

反応条件

温度
100 °C

実験手順

Triphenylphosphine (19 mg, 0.0735 mmol), water (2.9 mL), n-propanol (14.3 mL), aqueous sodium carbonate (9.8 mL of 2 M), and palladium (II) acetate (5.50 mg, 0.0245 mmol) were added to a mixture of 5-iodo-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile (2.59 g, 8.17 mmol) and 2-aminophenylboronic acid hydrochloride (1.70 g, 9.80 mmol). The reaction vessel was evacuated and filled with nitrogen three times and then heated under nitrogen at 100° C. for 24 hours. The work-up procedure described in Example 4 was followed with the modification that the reaction mixture was partitioned between chloroform and brine, and the extractions of the aqueous fraction were carried out with chloroform. After the organic fractions were combined, 2.75 g of 5-(2-aminophenyl)-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile were obtained as a brown solid.

後処理

  1. customThe reaction vessel was evacuated
  2. additionfilled with nitrogen three times
  3. customwas partitioned between chloroform and brine
  4. extractionthe extractions of the aqueous fraction

出典と根拠

ORDレコード
ord-b73eacb80b844f4a8575b57853a99aa3
出典データセット
uspto-grants-2012_05
特許番号
US08168802B2

反応ノート

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