Sodium Hydroxide → 1-(t-Butoxycarbonyl)-4-(6-phenyl-imidazo[1,2-a]pyridin-3-yl)-piperidine

HRID 1068220Notes

Reaction equation

HRID 1068220 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].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=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]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[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

7

Reactant 3

HCID 14798Sodium HydroxideHCID 66827Phenylboronic AcidHCID 211930311-(t-Butoxycarbonyl)-4-(6-bromo-imidazo[1,2-a]pyridin-3-yl)-piperidine

Product 1

HCID 211930351-(t-Butoxycarbonyl)-4-(6-phenyl-imidazo[1,2-a]pyridin-3-yl)-piperidineYield 118.4%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 120 mg of 1-(t-butoxycarbonyl)-4-(6-bromo-imidazo[1,2-a]pyridin-3-yl)-piperidine and 78 mg of phenylboronic acid in 5 mL of toluene and 2.5 mL of ethanol was added 8 mg of tetrakis(triphenylphosphine)-palladium(0), followed by 0.85 mL of 1.25N sodium hydroxide solution. The reaction was stirred at 100° C. for 8 hours. The mixture was concentrated under reduced pressure and the mixture was partitioned between EtOAc and water. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine and dried over MgSO4. The residue was purified by flash chromatography with 50% EtOAc in hexanes followed by 100% EtOAc to give 141 mg of the title compound as a viscous oil, which was used in next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe mixture was partitioned between EtOAc and water
  3. extractionAqueous layer was extracted with EtOAc (3×)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by flash chromatography with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-c5fd3360578248449da9f851778310a0
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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