HCID 59424693, compound → HCID 59424634, compound

HRID 1711018Notes

Reaction equation

HRID 1711018 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:6]2[N:13]([CH2:14][O:15][CH3:16])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1>C(O)(=O)C.[Fe]>[F:1][C:2]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:6]2[N:13]([CH2:14][O:15][CH3:16])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 1

HCID 59424693HCID 59424693, compound

Product 1

HCID 59424634HCID 59424634, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To as solution of 244 (85 mg, 0.267 mmol) in acetic acid (8 mL) at 100° C., was added iron powder (75 mg, 1.34 mmol). The reaction mixture was stirred for 5 minutes, filtered through Celite® pad and concentrated to dryness; the residue was purified by flash chromatography, eluent DCM/MeOH (30:1) to afford title compound 245 (18 mg, 23% yield) as an orange solid. MS (m/z): 289.1 (M+1).

Workup

  1. filtrationfiltered through Celite® pad
  2. concentrationconcentrated to dryness
  3. customthe residue was purified by flash chromatography, eluent DCM/MeOH (30:1)

Sources & evidence

ORD record
ord-b512c427f06648029b55d509bcf2108d
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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