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

HRID 418606Notes

Reaction equation

HRID 418606 reaction equation
[Br:1][C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2Cl)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[OH:28]>O(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:28][C:20]2[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=2[F:18])[CH:3]=1

Participants

6

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 183827742-Bromo-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridineYield 71.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Procedure

A mixture of 49 (5.1 g, 20.5 mmol), potassium carbonate (5.65 g, 4 mmol) and 2-fluoro-4-nitrophenol (4.82 g, 30.7 mmol) was heated at 190° C. in Ph2O (25 ml) for 3 hrs. After cooling to room temperature it was diluted with DCM and filtered. The filtrate was concentrated and the residue was purified by column chromatography (eluent ethyl acetate/hexane 3:1) to afford title compound 50 as a yellow solid (5.4 g, 71% yield). 1H NMR (DMSO-d6) δ (ppm): 8.55 (d, J=5.28 Hz, 1H), 8.46 (dd, J=2.5 and 10.4 Hz, 1H), 8.19 (d, J=8.8 Hz, 1H), 7.87 (s, 1H), 7.72 (t, J=8.4 Hz), 6.99 (d, J=5.47 Hz, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by column chromatography (eluent ethyl acetate/hexane 3:1)

Sources & evidence

ORD record
ord-75a7b663572948aa9b33b0944fc3169b
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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