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

HRID 1920264노트

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HRID 1920264 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b73eacb80b844f4a8575b57853a99aa3
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168802B2

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