Ethanol → HCID 86611067, compound

HRID 1785598Notes

Reaction equation

HRID 1785598 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=O.C([OH:24])C.O1CCCC1>Cl.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[NH:15][C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:21]2[C:13]=1[CH:14]=[O:24]

Participants

6

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 57595680(2-Fluoro-5-nitrophenyl)(1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

Product 1

HCID 86611067HCID 86611067, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolvent

Procedure

Compound 295 (130 mg, 0.46 mmol) was suspended in 6 M hydrochloric acid (10.0 mL) and ethanol (5.0 mL) unser an atmosphere of nitrogen. Tetrahydrofuran (5.0 mL) was added to completely dissolve the compound. Iron (229 mg) was added to the mixture and the reaction was heated to reflux for 2.5 hours. The reaction was cooled and concentrated under reduced pressure. The solid was dissolved in ethyl acetate and washed with saturated sodium bicarbonate. The organic portions were dried with anhydrous magnesium sulfate and adsorbed onto silica and purified by silica gel flash chromatography using 3% methanol:dichloromethane. The appropriate fractions were combined and concentrated to provide compound 296 as a pure white solid characterized by MS and 1H-NMR (33.9 mg, LRMS (ESI) [M+H+]+=256.1, [M−H+]−=254.1).

Workup

  1. dissolutionto completely dissolve the compound
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 2.5 hours
  4. temperatureThe reaction was cooled
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe solid was dissolved in ethyl acetate
  7. washwashed with saturated sodium bicarbonate
  8. dry with materialThe organic portions were dried with anhydrous magnesium sulfate
  9. custompurified by silica gel flash chromatography
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7199abe6a749449a9caa0f498e281032
Source dataset
uspto-grants-2009_03
Patent number
US07504509B2

Reaction notes

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