2-(Tributylstannyl)pyridine → HCID 57889253, compound

HRID 1820222Notes

Reaction equation

HRID 1820222 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:36])[NH:13][C@H:14]([CH:33]([CH3:35])[CH3:34])[C:15]([N:17]2[CH2:22][CH2:21][C@@:20]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)([OH:23])[C:19]([CH3:32])([CH3:31])[CH2:18]2)=[O:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([Sn](CCCC)(CCCC)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=1)CCC>C1(C)C=CC=CC=1.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C@@:20]2([OH:23])[CH2:21][CH2:22][N:17]([C:15](=[O:16])[C@H:14]([NH:13][C:12]([C:10]3[CH:9]=[C:4]([CH:3]=[C:2]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)[CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])=[O:36])[CH:33]([CH3:35])[CH3:34])[CH2:18][C:19]2([CH3:31])[CH3:32])=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 57889220HCID 57889220, compound

Product 1

HCID 57889253HCID 57889253, compoundYield 75.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Methyl 3-bromo-5-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamoyl)benzoate (40 mg, 0.069 mmol) was dissolved in toluene (3 mL) at 25° C. then 2-(tributylstannyl)pyridine (76 mg, 0.207 mmol) was added. The reaction was degassed then placed under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (4 mg, 3.45 μmol) was added and the reaction heated at reflux for 2 hours. The reaction was concentrated in vacuo to give a dark residue which was then dissolved in MeOH, filtered to remove insoluble material, then purified by LCMS HPLC. The obtained colorless oil was dissolved in EtOAc, dried over sodium sulfate and concentrated in vacuo to give methyl 3-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamoyl)-5-(pyridin-2-yl)benzoate (30 mg, 0.052 mmol, 75% yield) as a white glass. MS found: (M+H)+=578.34.

Workup

  1. customThe reaction was degassed
  2. temperaturethe reaction heated
  3. temperatureat reflux for 2 hours
  4. concentrationThe reaction was concentrated in vacuo
  5. customto give a dark residue which
  6. filtrationfiltered
  7. customto remove insoluble material
  8. custompurified by LCMS HPLC
  9. dissolutionThe obtained colorless oil was dissolved in EtOAc
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aacc9cc5f3424c36844ad0ed7eb23a74
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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