1,10-Phenanthroline → Methyl 3-{[2-(4-amino-furazan-3-yl)-1-phenyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}benzoate

HRID 1986370Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:17]3[C:18]([NH2:22])=[N:19][O:20][N:21]=3)[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[OH:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cu]I>[NH2:22][C:18]1[C:17]([C:9]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]3[CH:3]=[C:2]([O:23][C:24]4[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=4)[C:27]([O:29][CH3:30])=[O:28])[N:7]=[CH:6][C:5]=3[N:8]=2)=[N:21][O:20][N:19]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A heterogeneous mixture of the product from Step 7 (0.75 g, 2.1 mmol), methyl 3-hydroxybenzoate (1.5 equiv), 1,10-phenanthroline (1.5 equiv), copper (I) iodide (0.42 g, 2.2 mmol) and cesium carbonate (1.44 g, 3.78 mmol) in toluene (30 mL) and ethyl acetate (1.5 mL) was heated in a sealed tube at 125° C. for 2 days. The reaction mixture was cooled to rt triturated with ethyl acetate. The resulting crude solid was crystallized from ethanol to afford the title compound (0.30 g, 33%). MS (ES+) m/e 429 [M+H]+.

Workup

temperatureThe reaction mixture was cooled to rt
customtriturated with ethyl acetate
customThe resulting crude solid was crystallized from ethanol

Sources & evidence

ORD record: ord-2979f75db831494eb35b0342a77cbe01
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

Loading…