Pyrrolidine → HCID 68469316, compound

HRID 503016Notes

Reaction equation

HRID 503016 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:14]([CH3:27])[C:15]([C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)([CH3:20])[CH3:19])=[N:16][N:17]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:20][C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)([C:15]1[N:14]([CH3:27])[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:17][N:16]=1)[CH3:19]

Participants

8

Reactant 4

HCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 11523287HCID 11523287, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 68469316HCID 68469316, compound

Reagents, catalysts & solvents 3

HCID 66545394HCID 66545394, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A toluene solution (3.0 ml) of pyrrolidine (0.100 ml) was added to a mixture of 2-{1-[5-(2-bromophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}pyridine (360 mg), sodium tert-butoxide (136 mg), bis(dibenzylideneacetone)dipalladium (23.1 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (31.4 mg) under a nitrogen condition, followed by stirring at 100° C. for 18 hours. The reaction solution was diluted with water (15 ml) and then extracted with ethyl acetate (15 ml). The organic layer washed with brine, dried over anhydrous magnesium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=90:10) and further purified by preparative thin layer chromatography (hexane:acetone=1:1) to obtain 81.4 mg of 2-(1-methyl-1-{4-methyl-5-[2-(1-pyrrolidinyl)phenyl]-4H-1,2,4-triazol-3-yl]ethyl}pyridine (pale yellow crystals).

Workup

  1. extractionextracted with ethyl acetate (15 ml)
  2. washThe organic layer washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=90:10)
  7. customfurther purified by preparative thin layer chromatography (hexane:acetone=1:1)

Sources & evidence

ORD record
ord-f24347ad580e47a6b9d00f3a9ab3e115
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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