2-Fluoro-4-nitrophenol → HCID 58790417, compound

HRID 2193797Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][C:14](=[O:25])[N:15]([CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=3)[S:10][C:3]=12.[F:26][C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[OH:36].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:26][C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[O:36][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][C:14](=[O:25])[N:15]([CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=3)[S:10][C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the pyridone 414 (236 mg, 0.63 mmol) in Ph2O (1.3 mL) was added 2-fluoro-4-nitrophenol (197 mg, 1.26 mmol) and K2CO3 (173 mg, 1.26 mmol). The mixture was stirred at 100° C. for 1 h, then at 180° C. for 2 h, cooled and evaporated under reduced pressure. The residue was purified by flash chromatography with a gradient of methanol (2-10%) in dichloromethane to give title compound 415 (81 mg, 26% yield). MS (m/z): 498.0 (M+H). 1H NMR (DMSO-d6) δ (ppm): 9.16 (d, J=3.3 Hz, 1H), 8.66 (d, J=3.3 Hz, 1H), 8.60 (d, J=5.3 Hz, 1H), 8.47 (dd, J=10, 2.5 Hz, 1H), 8.19 (d, J=8.8 Hz, 1H), 8.02 (s, 1H), 7.69 (t, J=8.6 Hz, 1H), 6.98 (d, J=5.3 Hz, 1H), 4.02 (t, J=5.5 Hz, 2H), 3.58-3.43 (m, 4H), 2.59 (t, J=5.5 Hz, 2H), 2.50-2.41 (m, 4H).

Workup

waitat 180° C. for 2 h
temperaturecooled
customevaporated under reduced pressure
customThe residue was purified by flash chromatography with a gradient of methanol (2-10%) in dichloromethane

Sources & evidence

ORD record: ord-6fdb92ed9c3f4eaea48576127274a816
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329726B2

Reaction notes

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