HCID 117839581, compound → HCID 83855568, compound

HRID 1477658Notes

Reaction equation

HRID 1477658 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:16])[CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=2)=[CH:4][CH:3]=1>[Pt]=O.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:9]([CH3:16])[CH2:10][CH:11]([NH2:13])[CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 117839581HCID 117839581, compound

Product 1

HCID 83855568HCID 83855568, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To 2-(4-fluorophenyl)-1-methyl-4-nitro-1H-pyrrole (200 mg, 1.03 mmol) synthesized in Reference Synthesis Example 246, acetic acid (2.0 mL) and platinum oxide (20.0 mg) were added and the resultant solution was stirred under hydrogen atmosphere at room temperature for 3 days. After completion of the reaction, the reaction solution was filtered with Celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel (amino-based) column chromatography (chloroform/methanol=1/0→1/1) to obtain the title compound (15.0 mg, yield 7%).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. filtrationthe reaction solution was filtered with Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel (amino-based) column chromatography (chloroform/methanol=1/0→1/1)

Sources & evidence

ORD record
ord-cde0c952a96d422190f334861ad871ec
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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