Pyrrolidine → HCID 11561110, compound

HRID 2355783Notes

Reaction equation

HRID 2355783 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:5]=[CH:4][C:3]=1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 59753133HCID 59753133, compound

Product 1

HCID 11561110HCID 11561110, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

50 mg 2-[4-(2-Chloro-4-fluoro-benzenesulfonyl)-phenyl]-1,1,1-trifluoro-propan-2-ol (0.13 mmol, prepared as in the previous examples) was combined in a pressure tube with 50 mg pyrrolidine. The resulting mixture was then placed into a preheated 100° C. bath. After stirring for 12 h, the mixture was diluted with 10 mL CH2Cl2 and sat. NaHCO3, then extracted (3×10% MeOH/CH2Cl2). The organics were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 25% EtOAc/Hexanes) gave 35 mg of the product as a white solid (0.08 mmol). 1H NMR (CDCl3, 400 MHz) δ 8.09 (d, J=8.4 Hz, 1H), 7.92 (d, J=7.6 Hz, 2H), 7.70 (d, J=7.8 Hz, 2H), 6.49 (m, 2H), 3.32 (s, 4H), 2.04 (s, 4H), 1.78 (m, 3H).

Workup

  1. customwas then placed into a preheated 100° C.
  2. extractionextracted (3×10% MeOH/CH2Cl2)
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (SiO2, 25% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-96f772ef7f804867992649f4becb5ff6
Source dataset
uspto-grants-2010_07
Patent number
US07754890B2

Reaction notes

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