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

HRID 1341236Notes

Reaction equation

HRID 1341236 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>CC1=CC(C)=[O]->[Pd]2([O]1)[O]C(C)=CC(C)=[O]->2.COCCOCCOC.O=P([O-])([O-])[O-].[K+].c1ccc(P(c2ccccc2)[c]23->[Fe+2]456789%10(<-[cH]([cH]->4[cH-]->52)[cH]->63)<-[cH]2[cH]->7[cH-]->8[c]->9(P(C3C4CC5CC(C4)CC3C5)C3C4CC5CC(C4)CC3C5)[cH]->%102)cc1>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 178420528HCID 178420528, compoundCatalystHCID 178427257HCID 178427257, 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-75f2a91d5edd4fcca7b91793cf42c542
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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