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

HRID 1920264Notes

Reaction equation

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]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-b73eacb80b844f4a8575b57853a99aa3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168802B2

Reaction notes

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