Allyltributylstannane → 1-(t-Butoxycarbonyl)-4-(6-allyl-imidazo[1,2-a]pyridin-3-yl)-piperidine

HRID 1068222Notes

Reaction equation

HRID 1068222 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]3[CH:19]=[C:20](Br)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([Sn](CCCC)(CCCC)CC=C)[CH2:25][CH2:26]C>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]3[CH:19]=[C:20]([CH2:26][CH:25]=[CH2:24])[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 211930311-(t-Butoxycarbonyl)-4-(6-bromo-imidazo[1,2-a]pyridin-3-yl)-piperidine

Product 1

HCID 211930621-(t-Butoxycarbonyl)-4-(6-allyl-imidazo[1,2-a]pyridin-3-yl)-piperidineYield 63.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 89 mg of 1-(t-butoxycarbonyl)-4-(6-bromo-imidazo [1,2-a]pyridin-3-yl)-piperidine (from Example 274, Step A) and 158 mg tributyl(allyl)tin in 6 mL of toluene was added 5.0 mg of dichlorobis (triphenyl phosphine)-palladium(II). The mixture was refluxed for 8 hours. The reaction was cooled down to r.t. and partitioned between CH2Cl2 and water. Aqueous layer was extracted with CH2Cl2 (3×). The combined organic phase was washed with brine and dried over MgSO4. After concentration, the residue was purified by prep TLC (100% EtOAc) to afford 51 mg of a viscous oil.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. custompartitioned between CH2Cl2 and water
  3. extractionAqueous layer was extracted with CH2Cl2 (3×)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationAfter concentration
  7. customthe residue was purified by prep TLC (100% EtOAc)

Sources & evidence

ORD record
ord-0e7e8c96fba64c4da0fc8d3b53db8d2f
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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