Tetrahydrofuran → 4,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)dibenzene-1,2-diamine

HRID 2364789Notes

Reaction equation

HRID 2364789 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([N+:20]([O-])=O)[CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([N+:30]([O-])=O)[CH:24]=2)=[CH:4][CH:3]=1.C1COCC1>CN(C=O)C.[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:9]([C:23]3[CH:24]=[C:25]([NH2:30])[C:26]([NH2:27])=[CH:28][CH:29]=3)[CH2:10][CH2:11][CH:12]2[C:13]2[CH:14]=[C:15]([NH2:20])[C:16]([NH2:17])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 596167834,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)bis(2-nitroaniline)

Product 1

HCID 596166404,4'-(1-(4-Fluorophenyl)pyrrolidine-2,5-diyl)dibenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6228DimethylformamideSolvent

Procedure

The product from Example 29C (0.218 g, 0.50 mmol) was dissolved in DMF (5 mL) then platinum oxide (0.226 g, 0.99 mmol) was added via THF slurry. The flask was evacuated and purged with nitrogen twice, then evacuated and opened to hydrogen balloon. The mixture was stirred at room temperature for 20 h. The solution was taken on to the next step without purification.

Workup

  1. customThe flask was evacuated
  2. custompurged with nitrogen twice
  3. customevacuated
  4. customThe solution was taken on to the next step without purification

Sources & evidence

ORD record
ord-524bf80566984f5b9a1a20de7ca650db
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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