HCID 68694669, compound → HCID 68695543, compound

HRID 1711015Notes

Reaction equation

HRID 1711015 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)=[O:15])[S:13][C:6]=12>C(O)(=O)C.[Fe]>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([CH2:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]([C:16]4[O:17][CH:18]=[CH:19][CH:20]=4)=[O:15])[S:13][C:6]=23)=[C:2]([F:1])[CH:24]=1

Participants

4

Reactant 1

HCID 68694669HCID 68694669, compound

Product 1

HCID 68695543HCID 68695543, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To as solution of 240 (20 mg, 0.052 mmol) in acetic acid (2 mL) at 100° C., was added iron powder (15 mg, 0.260 mmol). The reaction mixture was stirred for 3 minutes, filtered through a celite pad and concentrated under reduced pressure. The residue was purified by flash chromatography, eluent EtOAc/hexane (3:7) to afford title compound 241 (3.3 mg, 18% yield) as a yellow solid. MS (m/z): 355.1 (M+1).

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography, eluent EtOAc/hexane (3:7)

Sources & evidence

ORD record
ord-cbb0555f2b0441bda8d4e7bb4414626b
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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