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

HRID 418570Notes

Reaction equation

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

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 7-chloro-2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridine (7) (1.0 g, 4 mmol), 2-fluoro-4-nitrophenol (0.942 g, 6 mmol) and K2CO3 (1.1 g, 8 mmol) in Ph2O (20 mL) was stirred at 200° C. for 24 h. The cooled reaction mixture was diluted with DCM (200 mL) and extracted with 1M HCl (200 mL). The aqueous phase was filtered through paper filter, basified (pH˜10) with conc. NH4OH to produce a cloudy mixture that was extracted with DCM. The organic phase was dried over anhydrous Na2SO4 and concentrated under pressure to give title compound 8 as an orange solid (0.667 g, 45% yield). MS (m/z): 371.0 (M+H).

Workup

customThe cooled reaction mixture
extractionextracted with 1M HCl (200 mL)
filtrationThe aqueous phase was filtered through paper
filtrationfilter
customto produce a cloudy mixture that
extractionwas extracted with DCM
dry with materialThe organic phase was dried over anhydrous Na2SO4
concentrationconcentrated under pressure

Sources & evidence

ORD record: ord-2fd90d224b214be18e947579513b1bc3
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093264B2

Reaction notes

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