HCID 59424576, compound → HCID 59424696, compound

HRID 1711025Notes

Reaction equation

HRID 1711025 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:6]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1>C(O)(=O)C.[Fe]>[F:1][C:2]1[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:6]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 1

HCID 59424576HCID 59424576, compound

Product 1

HCID 59424696HCID 59424696, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 253 (71.4 mg, 0.21 mmol) in acetic acid (2.1 mL) at 100° C., was added iron powder (59 mg, 1.05 mmol). The reaction mixture was stirred for 5 minutes, filtered through a Celite® pad and concentrated under reduced pressure. The residue was purified by column chromatography, eluent EtOAc/hexane (2:1), to afford title compound 254 (27.9 mg, 40% yield). MS (m/z): 321.1 (M+1).

Workup

  1. filtrationfiltered through a Celite® pad
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography, eluent EtOAc/hexane (2:1)

Sources & evidence

ORD record
ord-bc43bfc2acc04a938b2a162126b26314
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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