2-Fluoro-4-nitrophenol → 2-(1-Ethyl-1H-imidazol-5-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

HRID 2193701Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:15]([CH2:16][CH3:17])[CH:14]=[N:13][CH:12]=3)[S:10][C:3]=12.[F:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[OH:28].C(=O)([O-])[O-].[K+].[K+].CO.C(Cl)Cl>O(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:16]([N:15]1[C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:28][C:20]3[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=3[F:18])[CH:8]=2)=[CH:12][N:13]=[CH:14]1)[CH3:17]

Participants

Conditions

Temperature: 195 °C

Procedure

To a solution of 118 (4 g, 15.16 mmol) in Ph2O (60 ml) was added 2-fluoro-4-nitrophenol (4.76 g, 30.33 mmol) and potassium carbonate (8.38 g, 60.66 mmol). The reaction mixture was heated to 195° C. for 18 hrs the cooled to room temperature. The residue was purified by column chromatography (eluents EtOAc/Hex (9/1 to 5/5) then MeOH/CH2Cl2 (98/2)), to afford title compound 119 (3.05 g, 52% yield) as a yellow solid. MS (m/z): 385.0 (M+H).

Workup

temperaturecooled to room temperature
customThe residue was purified by column chromatography (eluents EtOAc/Hex (9/1 to 5/5)

Sources & evidence

ORD record: ord-e04339f8a6774d829460e3ae04178319
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329726B2

Reaction notes

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