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

HRID 2193734Notes

Reaction equation

HRID 2193734 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH:11]=[O:12])[S:10][C:3]=12.[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[OH:23].C([O-])([O-])=O.[K+].[K+].O(C1C=CC=CC=1)C1C=CC=CC=1>O.CCOC(C)=O>[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[O:23][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH:11]=[O:12])[S:10][C:3]=12

Participants

6

Reactant 4

HCID 7583Diphenyl EtherHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 509888497-Chlorothieno[3,2-b]pyridine-2-carbaldehyde

Product 1

HCID 587903817-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carbaldehydeYield 46.2%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of aldehyde 232 (500 mg, 2.53 mmol), 2-fluoro-4-nitrophenol (595 mg, 3.79 mmol), K2CO3 (700 mg, 5.06 mmol) and Ph2O (3.4 mL) was stirred in a sealed tube for 12 h at 170° C. The mixture was suspended in a water/EtOAc mixture, sonicated a few minutes and filtered, the solid residue was washed successively with water, EtOAc and ether, giving crude 233 (500 mg, 1.17 mmol, 46% yield) that was used in the next step without further purification. MS (m/z): (M+1) 319.0 (14%), (M+MeOH+1) 351.0 (100%).

Workup

  1. customsonicated a few minutes
  2. filtrationfiltered
  3. washthe solid residue was washed successively with water, EtOAc and ether

Sources & evidence

ORD record
ord-5ad0aaf2107f4ce5a83b7fcd74c50d1a
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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