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

HRID 1337633Notes

Reaction equation

HRID 1337633 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>C1CCC2=NCCCN2CC1.CC(C)(C)c1ccc(C=[CH](c2ccc(C(C)(C)C)cc2)->[Ni](<-[CH](=Cc2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)<-[CH](=Cc2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)cc1.CS(C)=O.c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)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 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 634876Binap, (A+-)-CatalystHCID 178440864HCID 178440864, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

Conditions

Temperature
30 °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-415e708014c14b9d869a147377241198
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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