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

HRID 1711042Notes

Reaction equation

HRID 1711042 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[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[CH:12][NH:13][C:6]=12>CC(O)=O.[Fe]>[NH:13]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:2]=2[F:1])[CH:11]=[CH:12]1

Participants

4

Reactant 1

HCID 594245967-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 594245934-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 267 (35 mg, 0.13 mmol) in AcOH (1 mL) at 90° C., was added iron powder (36 mg, 0.65 mmol). The reaction mixture was stirred vigorously for 10 min, cooled, filtered through a Celite pad and concentrated. The residue was partitioned between DCM and NaHCO3 saturated solution. Phases were separated; the aqueous phase was neutralized with AcOH and extracted with DCM. Primary organic phase and the extract were combined and concentrated to give the title compound 268 (31 mg, 99%) 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 partitioned between DCM and NaHCO3 saturated solution
  5. customPhases were separated
  6. extractionextracted with DCM
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b616fad2ed314e179c764bdc11e259dc
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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