3-Bromopyridine → 3-(4-Phenyl-1-piperidinyl)pyridine

HRID 1341286Notes

Reaction equation

HRID 1341286 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>CC(=O)[O][Pd][O]C(C)=O.CC(C)P(C(C)C)[c]12->[Fe+2]3456789(<-[cH]([cH]->3[cH-]->41)[cH]->52)<-[cH]1[cH]->6[cH-]->7[c]->8(P(C2C3CC4CC(C3)CC2C4)C2C3CC4CC(C3)CC2C4)[cH]->91.COCCOCCOC.O=P([O-])([O-])[O-].[K+]>c1ccc(C2CCN(c3cccnc3)CC2)cc1

Participants

9

Reactant 2

HCID 122863-BromopyridineHCID 698734-Phenylpiperidine

Product 3

HCID 2519CaffeineHCID 1223802233-(4-Phenyl-1-piperidinyl)pyridineYield 0%HCID 1398883374-(4-Phenylpiperidin-1-yl)pyridineYield 0%

Reagents, catalysts & solvents 4

HCID 21226062CID 21226062ReagentHCID 167845palladium(II) acetateCatalystHCID 178460671HCID 178460671, compoundCatalystHCID 8150DiglymeSolvent5×

Conditions

Temperature
60 °C

Workup

  1. customThe foil sealing tape was removed from the plate.
  2. addition3 μL of a 0.0667 M solution of caffeine in DMSO was added to each reaction well using an SPT Labtech Mosquito® liquid handling robot
  3. filtrationThe plates were then centrifuged for 15 to 20 seconds. · Keep liquid
  4. aliquotFollowing centrifugation, 500 nL of the resultant mixture from each well was carefully dispensed into four 384-well analytical plates (Analytical Sales # 38435) using an SPT Labtech Mosquito® liquid handling robot. Each well of these analytical plates contained 30 μL of DMSO with 0.1% acetic acid, pre-dosed by OpenTrons, to facilitate analysis.

Sources & evidence

ORD record
ord-fbc2f3244c3c4133b339a941d131b102
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
Original link
View source

Reaction notes

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