Diphenyl Ether → 7-(2-fluoro-4-nitrophenoxy)-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide

HRID 418673Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([NH:13][N:14]([CH3:16])[CH3:15])=[O:12])[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]([NH:13][N:14]([CH3:16])[CH3:15])=[O:12])[S:10][C:3]=12

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 7-chloro-N′,N′-dimethylthieno[3,2-b]pyridine-2-carbohydrazide (237) (798 mg, 3.13 mmol), 2-fluoro-4-nitrophenol (740 mg, 4.70 mmol), K2CO3 (830 mg, 6.26 mmol) and Ph2O (4.2 mL) was stirred in a sealed tube for 12 h at 170° C. The mixture was diluted with DCM, extracted with water, the organic phase dried with anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography (EtOAc/hexanes 1:1) giving 238 (772.5 mg, 2.05 mmol, 66% yield) as a brown foam. MS (m/z): (M+1) 377.0 (100%).

Workup

extractionextracted with water
dry with materialthe organic phase dried with anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by flash chromatography (EtOAc/hexanes 1:1)

Sources & evidence

ORD record: ord-785022e9e0f84d6c85883bf91e7ca03f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093264B2

Reaction notes

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