Pyrrolidine → 7-Fluoro-5-methyl-6-phenyl-2-(pyrrolidin-1-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17407Notes

Reaction equation

HRID 17407 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.[CH:21]([N:24]([CH:27]([CH3:29])C)CC)([CH3:23])C.N1CCCC1>ClCCl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([N:24]1[CH2:21][CH2:23][CH2:29][CH2:27]1)=[N:6]2

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685847937-Fluoro-5-methyl-6-phenyl-2-(pyrrolidin-1-yl)-1,3-benzoxazole-4-carbonitrileYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.13 g, 0.45 mmol) was dissolved in dichloromethane (10 ml), and diisopropylethylamine (92.0 μl, 0.54 mmol) and pyrrolidine (41.0 μl, 0.50 mmol) were added. This was heated under reflux for 4 hours, and diluted with dichloromethane. After washing with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=100:1) to obtain a pale yellow oil (0.14 g, 98%).

Workup

  1. temperatureThis was heated
  2. temperatureunder reflux for 4 hours
  3. washAfter washing with water
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-432e36890145439db80a17a276e7ffaa
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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