2-Fluoro-4-nitrophenol → 7-(2-fluoro-4-nitrophenoxy)-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamide

HRID 1261189Notes

Reaction equation

HRID 1261189 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[S:10][C:3]=12.C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[OH:32].CO.CCOC(C)=O>C1(OC2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[F:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[O:32][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[S:10][C:3]=12

Participants

7

Reactant 4

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 21584119Ethylacetate methanolHCID 221435377-Chloro-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamide

Product 1

HCID 594244757-(2-fluoro-4-nitrophenoxy)-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamideYield 41.2%

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5 (1.65 g, 6.85 mmol), potassium carbonate (5.68 g, 41.1 mmol) and 2-fluoro-4-nitrophenol (1.65 g, 10.3 mmol) were heated to 170° C. in diphenyl ether (20 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 (eluents EtOAc-hexane 9:1, then MeOH-EtOAc 1:4) to afford 6 as a yellow solid (1.02 g, 41% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.64 (d, J=5.3 Hz, 1H), 8.46 (dd, J=2.8 and 10.3 Hz, 1H), 8.20 (ddd, J=1.3 and 2.6 and 9.0 Hz, 1H), 7.98 (s, 1H), 7.73 (dd, J=8.3 Hz, 1H), 6.99 (dd, J=0.9 and 4.8 Hz, 1H), 3.25-3.30 (m, 3H), 3.02-3.11 (m, 3H).

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 (eluents EtOAc-hexane 9:1

Sources & evidence

ORD record
ord-03cf85ddf4bb4a5caafc7614ee943a0a
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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