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

HRID 1341064Notes

Reaction equation

HRID 1341064 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>CC(C)(C)[O-].COCCOCCOC.F[B-](F)(F)F.[Cu][I].[Na+].c1c[n+](C23CC4CC(CC(C4)C2)C3)cn1C12CC3CC(CC(C3)C1)C2>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 23676156Sodium t-butoxideReagentHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 162181051,3-Di(tricyclo[3.3.1.1~3,7~]decan-1-yl)-1H-imidazol-3-ium tetrafluoroborateCatalystHCID 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-1fa0d9ed15da4728812551f3703e070a
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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