1,10-Phenanthroline → 3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenol

HRID 1986374Notes

Reaction equation

C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)(C)(C)C.Br[C:17]1[N:22]=[CH:21][C:20]2[N:23]=[C:24]([C:28]3[C:29]([NH2:33])=[N:30][O:31][N:32]=3)[N:25]([CH2:26][CH3:27])[C:19]=2[CH:18]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[NH2:33][C:29]1[C:28]([C:24]2[N:25]([CH2:26][CH3:27])[C:19]3[CH:18]=[C:17]([O:6][C:7]4[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=4)[N:22]=[CH:21][C:20]=3[N:23]=2)=[N:32][O:31][N:30]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The product from Step 1 (46 mg, 0.20 mmol) in toluene (10 mL) was treated with the product from Step 2 (42 mg, 0.14 mmol), cuprous iodide (26 mg, 0.14 mmol), 1,10-phenanthroline (43 mg, 0.24 mmol), and cesium carbonate (88 mg, 0.27 mmol). The resulting mixture was heated to 120° C. for 48 hours in a sealed tube. After concentration the residue was purified by reverse phase HPLC to give the title compound (3.3 mg, 7%). MS (ES+) m/e 339 [M+H]+.

Workup

concentrationAfter concentration the residue
customwas purified by reverse phase HPLC

Sources & evidence

ORD record: ord-e1cbc58a817a4abe81eebe57cd48ce10
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

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