2-Fluoro-4-nitrophenol → 7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

HRID 2193638Notes

Reaction equation

HRID 2193638 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[OH:27]>C1(OC2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[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]=[CH:9][S:10][C:3]=12

Participants

6

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 112752517-Chlorothieno[3,2-b]pyridine

Product 1

HCID 594246827-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridineYield 77.1%

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2 (500 mg, 2.95 mmol), potassium carbonate (1.62 g, 11.8 mmol) and 2-fluoro-4-nitrophenol (603 mg, 3.85 mmol) were heated to 170° C. in diphenyl ether (10 ml) for 5 hrs. The mixture was cooled to room temperature, diluted with EtOAc and washed with water. The organic phase was collected, dried over anhydrous sodium sulfate and the solvents were removed under reduced pressure. The residue was purified by column chromatography, eluent gradient EtOAc-hexane (9:1) to EtOAc, to afford the title compound 3 (660 mg, 76% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.60 (d, J=5.54 Hz, 1H), 8.14 (m, 3H), 7.80 (d, J=5.47 Hz, 1H), 7.61 (d, J=5.48 Hz, 1H), 7.36 (t, J=7.63 Hz), 6.65 (m, 1H).

Workup

  1. washwashed with water
  2. customThe organic phase was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvents were removed under reduced pressure
  5. customThe residue was purified by column chromatography, eluent gradient EtOAc-hexane (9:1) to EtOAc

Sources & evidence

ORD record
ord-698f0034c7b64ebfb039dff01aca86ff
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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