7-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-c]pyridine → 4-(1H-Pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorobenzenamine

HRID 1711035Notes

Reaction equation

HRID 1711035 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[N:6]=[CH:7][CH:8]=[C:9]2[CH:13]=[CH:12][NH:11][C:10]=12>CC(O)=O.[Fe]>[NH:11]1[C:10]2=[C:5]([O:4][C:3]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:2]=3[F:1])[N:6]=[CH:7][CH:8]=[C:9]2[CH:13]=[CH:12]1

Participants

4

Reactant 1

HCID 594246417-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 594246294-(1H-Pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorobenzenamineYield 99.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 260 (100 mg, 0.36 mmol) in AcOH (4 mL) at 90° C., was added iron powder (102 mg, 2.1 mmol). The reaction mixture was vigorously stirred for 10 min, cooled, filtered through a Celite pad and concentrated. The residue was purified by flash column chromatography, eluent EtOAc/hexane (1:1), to afford title compound 261 (87 mg, 99% yield) as an off-white solid. MS (m/z): 244.1 (M+H) (found).

Workup

  1. temperaturecooled
  2. filtrationfiltered through a Celite pad
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography, eluent EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-f27097951d65493a9321f93e0585f95f
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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