Stannous Chloride → HCID 178507461, compound

HRID 250731Notes

Reaction equation

[Sn](Cl)Cl.[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[C:12]1[NH:13][C:14]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[C:25]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:24]=2)=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1>C(O)(=O)C.C(OCC)(=O)C>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[C:12]1[NH:13][C:14]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([NH:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:24]=2)=[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Add tin(II) chloride (0.11 g, 0.6 mmol) to a solution of 2-(2,6-difluorophenyl)-4-phenyl-5-(3-(benzyl)amino-4-nitrophenyl)imidazole (0.09 g, 0.2 mmol) in 10 mL acetic acid. Bubble nitrogen through the solution for 15 minutes and then heat at 90° C. for 1 hour under a nitrogen atmosphere. Cool the reaction mixture to room temperature, dilute with ethyl acetate, and then wash sequentially with 3:1 ammonium hydroxide:saturated aqueous ammonium chloride, saturated aqueous sodium chloride, and water. Dry the organic phase over magnesium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5:1 dichloromethane:acetonitrile to provide the title compound (0.05 g, 59%).

Workup

temperatureCool the reaction mixture to room temperature
washwash sequentially with 3:1 ammonium hydroxide
dry with materialDry the organic phase over magnesium sulfate
concentrationconcentrate under reduced pressure
washeluting with 5:1 dichloromethane

Sources & evidence

ORD record: ord-05a8f60a1fe4415a955c5f1c4e63d73f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863310B2

Reaction notes

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